497:
419:
139:). The double-bond character of the S−O bond may be accounted for by donation of electron density into C−S antibonding orbitals ("no-bond" resonance forms in valence-bond language). Nevertheless, due to its simplicity and lack of ambiguity, the IUPAC recommends use of the expanded octet double-bond structure to depict sulfoxides, rather than the dipolar structure or structures that invoke "no-bond" resonance contributors. The S–O interaction has an
31:
543:
156:
103:
118:
Sulfoxides feature relatively short S–O distances. In DMSO, the S–O distance is 1.531 Å. The sulfur center is pyramidal; the sum of the angles at sulfur is about 306°. Sulfoxides are generally represented with the structural formula R−S(=O)−R', where R and R' are organic groups. The bond
199:
is slow at room temperature. The enthalpy of activation for racemization is in the range 35 - 42 kcal/mol and the corresponding entropy of activation is -8 - +4 cal/mol-K. The barriers are lower for allylic and benzylic substituents.
328:
Sulfoxides undergo deoxygenation to give sulfides. Typically metal complexes are used to catalyze the reaction, using hydrosilanes as the stoichiometric reductant. The deoxygenation of dimethylsulfoxide is catalyzed by
1037:
Peyronneau M, Roques N, Mazières S, Le Roux C (2003). "Catalytic Lewis Acid
Activation of Thionyl Chloride: Application to the Synthesis of ArylSulfinyl Chlorides Catalyzed by Bismuth(III) Salts".
1226:
Cubbage, Jerry W.; Guo, Yushen; McCulla, Ryan D.; Jenks, William S. (1 December 2001). "Thermolysis of Alkyl
Sulfoxides and Derivatives: A Comparison of Experiment and Theory".
1321:
Armstrong, C.; Plant, M.A.; Scott, G. (February 1975). "Mechanisms of antioxidant action: the nature of the redox behaviour of thiodipropionate esters in polypropylene".
1212:
504:
496:
1393:
2312:
2317:
1305:
1185:
Michael
Carrasco, Robert J. Jones, Scott Kamel, H. Rapoport, Thien Truong (1992). "N-(Benzyloxycarbonyl)-L-Vinylglycine Methyl Ester".
969:
905:
491:
774:
Cunningham TP, Cooper DL, Gerratt J, Karadakov PB, Raimondi M (1997). "Chemical bonding in oxofluorides of hypercoordinate sulfur".
687:
224:
is a typical oxidant, but periodate has also been used. In these oxidations, care is required to avoid over oxidation to form the
1386:
1122:
Sousa SC, Fernandes AC (2015). "Efficient deoxygenation methodologies catalyzed by oxo-molybdenum and oxo-rhenium complexes".
2216:
268:
853:
Fernández I, Khiar N (September 2003). "Recent developments in the synthesis and utilization of chiral sulfoxides".
534:
of the metal, the sulfoxide binds through either the sulfur or the oxygen atom. The latter is particularly common.
2340:
1789:
1379:
1060:
Bandgar BP, Makone SS (2004). "Lithium/Sodium
Perchlorate Catalyzed Synthesis of Symmetrical Diaryl Sulfoxides".
1826:
2299:
184:
160:
1261:
Koelewijn, P.; Berger, H. (2 September 2010). "Mechanism of the antioxidant action of dialkyl sulfoxides".
1013:
2199:
394:
295:
Both aryl sulfinyl chlorides and diaryl sulfoxides can be also prepared from arenes through reaction with
75:
2306:
2194:
1206:
237:
180:
107:
51:
195:
is sufficiently high that sulfoxides are optically stable near room temperature. That is, the rate of
738:
Thomas R, Shoemaker CB, Eriks K (1966). "The
Molecular and Crystal Structure of Dimethyl Sulfoxide, (H
2275:
1720:
587:
527:
248:
2345:
1581:
479:
244:, thus their oxidation gives chiral sulfoxides. This process can be performed enantioselectively.
1139:
1077:
985:
Holland, Herbert Leslie (1988). "Chiral
Sulfoxidation by Biotransformation of Organic Sulfides".
835:
233:
172:
144:
87:
802:
2265:
2235:
1993:
1615:
1301:
1243:
1163:
1019:
965:
901:
870:
683:
362:
The α-CH groups of alkyl sulfoxides are susceptible to deprotonation by strong bases, such as
221:
209:
188:
71:
39:
482:. Structures based on thiodipropionate esters are popular. The reverse reaction is possible.
478:, but lack long-term stability. Some parent sulfoxides are therefore marketed as antioxidant
1970:
1464:
1402:
1357:
1330:
1293:
1270:
1235:
1194:
1131:
1104:
1069:
1042:
994:
957:
930:
893:
862:
825:
817:
783:
755:
720:
675:
642:
632:
554:
550:
418:
402:
296:
229:
63:
2189:
1948:
1943:
1926:
1909:
1710:
1459:
171:
of electrons resides on the sulfur atom, giving it tetrahedral electron-pair geometry and
409:
ester. The first step of the reaction sequence involves the sulfoxide oxygen acting as a
2260:
2255:
2131:
2126:
2121:
1914:
1881:
1665:
1647:
1637:
1297:
595:
363:
330:
272:
252:
136:
1348:
Calligaris M (2004). "Structure and
Bonding in Metal Sulfoxide Complexes: an Update".
621:"Oxidation of sulfides to chiral sulfoxides using Schiff base-vanadium (IV) complexes"
30:
2334:
2280:
2228:
2159:
2045:
2035:
2030:
2020:
2015:
1965:
1960:
1876:
1871:
1861:
1715:
1670:
1632:
1620:
1591:
1469:
1334:
1143:
647:
443:
217:
140:
1081:
839:
619:
Gama Á, Flores-López LZ, Aguirre G, Parra-Hake M, Hellberg LH, Somanathan R (2003).
2211:
2098:
2093:
2070:
1821:
1660:
1586:
1523:
1518:
1496:
1452:
1437:
1427:
573:
546:
431:
196:
192:
176:
637:
620:
2270:
2223:
2184:
2065:
1953:
1938:
1933:
1921:
1486:
1481:
1447:
1442:
1432:
1410:
1158:
581:
531:
475:
410:
132:
128:
961:
135:. The double-bond resonance form implies 10 electrons around sulfur (10-S-3 in
86:, a precursor to the compound that gives freshly crushed garlic its aroma, and
2179:
2170:
2050:
2005:
1901:
1866:
1856:
1796:
1732:
1655:
1603:
1361:
1135:
1108:
759:
724:
591:
577:
558:
1274:
1198:
934:
897:
2146:
2060:
2010:
1998:
1841:
1816:
1625:
821:
241:
168:
79:
1247:
874:
1073:
679:
542:
17:
2154:
2108:
2075:
1771:
1677:
1551:
1506:
1491:
1046:
405:
to give migration of the oxygen from sulfur to the adjacent carbon as an
998:
514:, a representative metal complex of a sulfoxide. Three DMSO ligands are
2116:
2040:
1891:
1886:
1851:
1836:
1831:
1801:
1784:
1608:
1535:
1501:
562:
406:
225:
213:
179:). When the two organic residues are dissimilar, the sulfur atom is a
91:
1239:
866:
830:
2204:
2136:
1980:
1689:
1682:
1576:
1557:
1546:
1530:
1476:
787:
606:
602:
439:
124:
120:
83:
67:
1371:
803:"Graphical representation standards for chemical structure diagrams"
155:
572:
The sulfoxide functional group occurs in several drugs. Notable is
2085:
2055:
1988:
1846:
1811:
1806:
1779:
1727:
1694:
1598:
1422:
711:
catalyst for C–H bond arylation of heteroarenes with haloarenes".
541:
495:
398:
154:
102:
101:
29:
674:. PATai's Chemistry of Functional Groups. John Wiley & Sons.
1513:
1023:
264:
1375:
1290:
Reference Module in
Materials Science and Materials Engineering
598:
catalyzes the interconversion of DMSO and dimethylsulfide.
594:
and its accumulation is associated with aging. The enzyme
703:
Yanagisawa S, Itami K (2011). "Palladium/2,2′-bipyridyl/Ag
557:
containing a sulfoxide functional group. The related drug
1095:
Shiri L, Kazemi M (2017). "Deoxygenation of
Sulfoxides".
921:
Johnson CR, Keiser JE (1966). "Methyl Phenyl
Sulfoxide".
106:
Structure of DMSO (red = O, yellow = S) as determined by
672:
Syntheses of Sulphones, Sulphoxides and Cyclic Sulphides
576:, the optically pure form of the proton-pump inhibitor
954:
E-EROS Encyclopedia of Reagents for Organic Synthesis
776:
Journal of the Chemical Society, Faraday Transactions
27:
Organic compound containing a sulfinyl group (>SO)
580:. Another commercially important sulfoxides include
299:
in the presence of Lewis acid catalysts such as BiCl
147:
character, with negative charge centered on oxygen.
2248:
2168:
2145:
2107:
2084:
1979:
1900:
1770:
1747:
1703:
1646:
1569:
1544:
1409:
1012:Audrieth, Ludwig F.; Kleinberg, Jacob (1953).
1018:. New York: John Wiley & Sons. p. 222.
175:shape (steric number 4 with one lone pair; see
948:Kagan HB, Chellappan SK, Lattanzi A (2015). "(
890:Ullmann's Encyclopedia of Industrial Chemistry
601:Naturally-occurring chiral sulfoxides include
1387:
1288:Kröhnke, C. (2016). "Polymer Stabilization".
430:Sulfoxide undergo thermal elimination via an
8:
1211:: CS1 maint: multiple names: authors list (
247:Symmetrical sulfoxides can be formed from a
74:functional group. Sulfoxides are oxidized
1767:
1566:
1394:
1380:
1372:
1263:Recueil des Travaux Chimiques des Pays-Bas
888:Roy KM (2002). "Sulfones and Sulfoxides".
530:with transition metals. Depending on the
829:
646:
636:
662:
263:In addition to the oxidation routes, di
82:. Examples of important sulfoxides are
1204:
208:Sulfoxides are typically prepared by
7:
670:Patai S, Rappoport Z, eds. (1995).
1298:10.1016/B978-0-12-803581-8.01487-9
526:Sulfoxides, especially DMSO, form
492:Transition metal sulfoxide complex
267:sulfoxides can be prepared by two
25:
143:aspect, resulting in significant
1228:The Journal of Organic Chemistry
952:)-(+)-Phenyl methyl sulfoxide".
417:
569:DMSO is a widely used solvent.
1350:Coordination Chemistry Reviews
1:
324:Deoxygenation and oxygenation
240:. Unsymmetrical sulfides are
1335:10.1016/0014-3057(75)90141-X
1159:"2,3-Diphenyl-1,3-Butadiene"
638:10.3998/ark.5550190.0004.b02
538:Applications and occurrence
216:, sometimes referred to as
127:atoms is intermediate of a
2362:
1173:, vol. 6, p. 531
962:10.1002/047084289X.rn00456
810:Pure and Applied Chemistry
590:forms from the amino acid
489:
2289:
1362:10.1016/j.ccr.2004.02.005
1136:10.1007/s11164-017-2976-6
1109:10.1016/j.ccr.2014.09.008
760:10.1107/S0365110X66002263
725:10.1016/j.tet.2011.03.093
648:2027/spo.5550190.0004.b02
1323:European Polymer Journal
1275:10.1002/recl.19720911102
1199:10.15227/orgsyn.070.0029
935:10.15227/orgsyn.046.0078
898:10.1002/14356007.a25_487
275:using an acid catalyst:
191:required to invert this
2300:chemical classification
892:. Weinheim: Wiley-VCH.
822:10.1351/pac200880020277
816:: 277–410 (on p. 389).
474:The acids are powerful
185:methyl phenyl sulfoxide
161:methyl phenyl sulfoxide
1157:Iwai I, Ide J (1988).
566:
528:coordination complexes
523:
518:-bonded to Ru, one is
486:Coordination chemistry
401:sulfoxides react with
395:Pummerer rearrangement
164:
115:
35:
2307:chemical nomenclature
1074:10.1081/SCC-120027723
680:10.1002/9780470666357
545:
499:
426:Elimination reactions
158:
108:X-ray crystallography
105:
98:Structure and bonding
52:organosulfur compound
33:
1047:10.1055/s-2003-38358
1015:Non-aqueous solvents
588:Methionine sulfoxide
532:hard-soft properties
251:compound and liquid
236:and then further to
1763:not C, H or O)
1097:Res. Chem. Intermed
999:10.1021/cr00085a002
480:polymer stabilisers
358:Acid-base reactions
333:, a molybdoenzyme:
2205:Hypervalent iodine
801:Brecher J (2008).
567:
524:
345:e + 2 H → SMe
234:dimethyl sulfoxide
183:, for example, in
173:trigonal pyramidal
165:
116:
88:dimethyl sulfoxide
36:
2341:Functional groups
2328:
2327:
2266:Sulfenyl chloride
2244:
2243:
1743:
1742:
1562:(only C, H and O)
1403:Functional groups
1307:978-0-12-803581-8
1269:(11): 1275–1286.
1240:10.1021/jo0160625
1234:(26): 8722–8736.
1187:Organic Syntheses
1171:Collected Volumes
1164:Organic Syntheses
867:10.1021/cr990372u
782:(13): 2247–2254.
719:(24): 4425–4430.
222:hydrogen peroxide
90:(DMSO), a common
40:organic chemistry
16:(Redirected from
2353:
2295:
2200:Trifluoromethoxy
1768:
1764:
1567:
1563:
1416:
1396:
1389:
1382:
1373:
1366:
1365:
1356:(3–4): 351–375.
1345:
1339:
1338:
1318:
1312:
1311:
1285:
1279:
1278:
1258:
1252:
1251:
1223:
1217:
1216:
1210:
1202:
1182:
1176:
1174:
1167:
1154:
1148:
1147:
1124:Coord. Chem. Rev
1119:
1113:
1112:
1092:
1086:
1085:
1057:
1051:
1050:
1041:(5): 0631–0634.
1034:
1028:
1027:
1009:
1003:
1002:
987:Chemical Reviews
982:
976:
975:
945:
939:
938:
918:
912:
911:
885:
879:
878:
855:Chemical Reviews
850:
844:
843:
833:
807:
798:
792:
791:
788:10.1039/A700708F
771:
765:
763:
748:Acta Crystallogr
735:
729:
728:
700:
694:
693:
667:
652:
650:
640:
555:enantiopure drug
551:blockbuster drug
421:
403:acetic anhydride
344:
297:thionyl chloride
238:dimethyl sulfone
230:dimethyl sulfide
228:. For example,
131:and a polarized
66:attached to two
64:functional group
61:
46:, also called a
21:
2361:
2360:
2356:
2355:
2354:
2352:
2351:
2350:
2331:
2330:
2329:
2324:
2293:
2285:
2240:
2195:Trichloromethyl
2190:Trifluoromethyl
2164:
2141:
2103:
2080:
1975:
1944:Phosphine oxide
1896:
1762:
1760:
1759:
1757:
1755:
1753:
1751:
1749:
1739:
1699:
1642:
1561:
1560:
1555:
1550:
1540:
1414:
1413:
1405:
1400:
1370:
1369:
1347:
1346:
1342:
1320:
1319:
1315:
1308:
1287:
1286:
1282:
1260:
1259:
1255:
1225:
1224:
1220:
1203:
1184:
1183:
1179:
1169:
1156:
1155:
1151:
1121:
1120:
1116:
1094:
1093:
1089:
1059:
1058:
1054:
1036:
1035:
1031:
1011:
1010:
1006:
984:
983:
979:
972:
947:
946:
942:
920:
919:
915:
908:
887:
886:
882:
861:(9): 3651–705.
852:
851:
847:
805:
800:
799:
795:
773:
772:
768:
745:
741:
737:
736:
732:
710:
706:
702:
701:
697:
690:
669:
668:
664:
659:
618:
615:
613:Further reading
540:
512:
508:
494:
488:
469:
465:
461:
457:
453:
438:to yield vinyl
435:
428:
389:
385:
381:
378:+ NaH → CH
377:
373:
360:
352:
348:
342:
340:
326:
321:
314:
310:
306:
302:
290:
286:
282:
261:
259:Aryl sulfoxides
232:is oxidized to
206:
159:Enantiomers of
153:
113:
100:
70:atoms. It is a
59:
34:Sulfoxide group
28:
23:
22:
15:
12:
11:
5:
2359:
2357:
2349:
2348:
2343:
2333:
2332:
2326:
2325:
2323:
2322:
2321:
2320:
2315:
2303:
2296:
2290:
2287:
2286:
2284:
2283:
2281:Sulfinylamines
2278:
2273:
2268:
2263:
2261:Phosphoramides
2258:
2256:Isothiocyanate
2252:
2250:
2246:
2245:
2242:
2241:
2239:
2238:
2233:
2232:
2231:
2221:
2220:
2219:
2209:
2208:
2207:
2202:
2197:
2192:
2187:
2176:
2174:
2166:
2165:
2163:
2162:
2157:
2151:
2149:
2143:
2142:
2140:
2139:
2134:
2132:Selenenic acid
2129:
2127:Seleninic acid
2124:
2122:Selenonic acid
2119:
2113:
2111:
2105:
2104:
2102:
2101:
2096:
2090:
2088:
2082:
2081:
2079:
2078:
2073:
2068:
2063:
2058:
2053:
2048:
2043:
2038:
2033:
2028:
2023:
2018:
2013:
2008:
2003:
2002:
2001:
1991:
1985:
1983:
1977:
1976:
1974:
1973:
1968:
1963:
1958:
1957:
1956:
1946:
1941:
1936:
1931:
1930:
1929:
1919:
1918:
1917:
1915:Phosphodiester
1906:
1904:
1898:
1897:
1895:
1894:
1889:
1884:
1879:
1874:
1869:
1864:
1859:
1854:
1849:
1844:
1839:
1834:
1829:
1824:
1819:
1814:
1809:
1804:
1799:
1794:
1793:
1792:
1787:
1776:
1774:
1765:
1761:(one element,
1745:
1744:
1741:
1740:
1738:
1737:
1736:
1735:
1725:
1724:
1723:
1718:
1707:
1705:
1701:
1700:
1698:
1697:
1692:
1687:
1686:
1685:
1675:
1674:
1673:
1668:
1663:
1652:
1650:
1644:
1643:
1641:
1640:
1638:Methylenedioxy
1635:
1630:
1629:
1628:
1623:
1613:
1612:
1611:
1606:
1596:
1595:
1594:
1584:
1579:
1573:
1571:
1564:
1542:
1541:
1539:
1538:
1533:
1528:
1527:
1526:
1521:
1511:
1510:
1509:
1504:
1499:
1494:
1489:
1484:
1474:
1473:
1472:
1467:
1457:
1456:
1455:
1450:
1445:
1440:
1435:
1430:
1419:
1417:
1415:(only C and H)
1407:
1406:
1401:
1399:
1398:
1391:
1384:
1376:
1368:
1367:
1340:
1329:(2): 161–167.
1313:
1306:
1280:
1253:
1218:
1177:
1149:
1114:
1087:
1068:(4): 743–750.
1052:
1029:
1004:
993:(3): 473–485.
977:
971:978-0471936237
970:
940:
923:Org. Syntheses
913:
907:978-3527306732
906:
880:
845:
793:
766:
743:
739:
730:
708:
704:
695:
688:
661:
660:
658:
655:
654:
653:
614:
611:
596:DMSO reductase
539:
536:
510:
506:
490:Main article:
487:
484:
472:
471:
467:
463:
459:
455:
451:
444:sulfenic acids
433:
427:
424:
423:
422:
391:
390:
387:
383:
379:
375:
371:
364:sodium hydride
359:
356:
355:
354:
350:
346:
338:
331:DMSO reductase
325:
322:
320:
317:
312:
308:
304:
300:
293:
292:
288:
284:
280:
273:sulfur dioxide
271:arylations of
269:Friedel–Crafts
260:
257:
253:sulfur dioxide
205:
202:
189:energy barrier
152:
149:
137:N-X-L notation
111:
99:
96:
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
2358:
2347:
2344:
2342:
2339:
2338:
2336:
2319:
2316:
2314:
2311:
2310:
2309:
2308:
2304:
2302:
2301:
2297:
2292:
2291:
2288:
2282:
2279:
2277:
2274:
2272:
2269:
2267:
2264:
2262:
2259:
2257:
2254:
2253:
2251:
2247:
2237:
2234:
2230:
2227:
2226:
2225:
2222:
2218:
2215:
2214:
2213:
2210:
2206:
2203:
2201:
2198:
2196:
2193:
2191:
2188:
2186:
2183:
2182:
2181:
2178:
2177:
2175:
2173:
2172:
2167:
2161:
2160:Telluroketone
2158:
2156:
2153:
2152:
2150:
2148:
2144:
2138:
2135:
2133:
2130:
2128:
2125:
2123:
2120:
2118:
2115:
2114:
2112:
2110:
2106:
2100:
2097:
2095:
2092:
2091:
2089:
2087:
2083:
2077:
2074:
2072:
2069:
2067:
2064:
2062:
2059:
2057:
2054:
2052:
2049:
2047:
2046:Sulfonic acid
2044:
2042:
2039:
2037:
2036:Sulfinic acid
2034:
2032:
2031:Thiosulfonate
2029:
2027:
2024:
2022:
2021:Thiosulfinate
2019:
2017:
2016:Sulfenic acid
2014:
2012:
2009:
2007:
2004:
2000:
1997:
1996:
1995:
1992:
1990:
1987:
1986:
1984:
1982:
1978:
1972:
1971:Phosphaallene
1969:
1967:
1966:Phosphaalkyne
1964:
1962:
1961:Phosphaalkene
1959:
1955:
1952:
1951:
1950:
1947:
1945:
1942:
1940:
1937:
1935:
1932:
1928:
1925:
1924:
1923:
1920:
1916:
1913:
1912:
1911:
1908:
1907:
1905:
1903:
1899:
1893:
1890:
1888:
1885:
1883:
1880:
1878:
1875:
1873:
1870:
1868:
1865:
1863:
1860:
1858:
1855:
1853:
1850:
1848:
1845:
1843:
1840:
1838:
1835:
1833:
1830:
1828:
1825:
1823:
1820:
1818:
1815:
1813:
1810:
1808:
1805:
1803:
1800:
1798:
1795:
1791:
1788:
1786:
1783:
1782:
1781:
1778:
1777:
1775:
1773:
1769:
1766:
1746:
1734:
1731:
1730:
1729:
1726:
1722:
1719:
1717:
1714:
1713:
1712:
1709:
1708:
1706:
1702:
1696:
1693:
1691:
1688:
1684:
1681:
1680:
1679:
1676:
1672:
1669:
1667:
1664:
1662:
1659:
1658:
1657:
1654:
1653:
1651:
1649:
1645:
1639:
1636:
1634:
1633:Ethylenedioxy
1631:
1627:
1624:
1622:
1619:
1618:
1617:
1614:
1610:
1607:
1605:
1602:
1601:
1600:
1597:
1593:
1590:
1589:
1588:
1585:
1583:
1580:
1578:
1575:
1574:
1572:
1568:
1565:
1559:
1553:
1548:
1543:
1537:
1534:
1532:
1529:
1525:
1522:
1520:
1517:
1516:
1515:
1512:
1508:
1505:
1503:
1500:
1498:
1495:
1493:
1490:
1488:
1485:
1483:
1480:
1479:
1478:
1475:
1471:
1468:
1466:
1463:
1462:
1461:
1458:
1454:
1451:
1449:
1446:
1444:
1441:
1439:
1436:
1434:
1431:
1429:
1426:
1425:
1424:
1421:
1420:
1418:
1412:
1408:
1404:
1397:
1392:
1390:
1385:
1383:
1378:
1377:
1374:
1363:
1359:
1355:
1351:
1344:
1341:
1336:
1332:
1328:
1324:
1317:
1314:
1309:
1303:
1299:
1295:
1291:
1284:
1281:
1276:
1272:
1268:
1264:
1257:
1254:
1249:
1245:
1241:
1237:
1233:
1229:
1222:
1219:
1214:
1208:
1200:
1196:
1192:
1188:
1181:
1178:
1172:
1166:
1165:
1160:
1153:
1150:
1145:
1141:
1137:
1133:
1129:
1125:
1118:
1115:
1110:
1106:
1103:: 6007–6041.
1102:
1098:
1091:
1088:
1083:
1079:
1075:
1071:
1067:
1063:
1062:Synth. Commun
1056:
1053:
1048:
1044:
1040:
1033:
1030:
1025:
1021:
1017:
1016:
1008:
1005:
1000:
996:
992:
988:
981:
978:
973:
967:
963:
959:
955:
951:
944:
941:
936:
932:
928:
924:
917:
914:
909:
903:
899:
895:
891:
884:
881:
876:
872:
868:
864:
860:
856:
849:
846:
841:
837:
832:
827:
823:
819:
815:
811:
804:
797:
794:
789:
785:
781:
777:
770:
767:
761:
757:
753:
749:
734:
731:
726:
722:
718:
714:
699:
696:
691:
689:9780470666357
685:
681:
677:
673:
666:
663:
656:
649:
644:
639:
634:
630:
626:
622:
617:
616:
612:
610:
608:
604:
599:
597:
593:
589:
585:
583:
579:
575:
570:
564:
560:
556:
552:
548:
544:
537:
535:
533:
529:
521:
517:
513:
502:
498:
493:
485:
483:
481:
477:
449:
448:
447:
445:
441:
437:
425:
420:
416:
415:
414:
412:
408:
404:
400:
396:
369:
368:
367:
365:
357:
336:
335:
334:
332:
323:
318:
316:
298:
278:
277:
276:
274:
270:
266:
258:
256:
254:
250:
249:diorganylzinc
245:
243:
239:
235:
231:
227:
223:
219:
218:sulfoxidation
215:
211:
203:
201:
198:
194:
190:
186:
182:
181:chiral center
178:
174:
170:
162:
157:
150:
148:
146:
142:
141:electrostatic
138:
134:
130:
126:
122:
109:
104:
97:
95:
93:
89:
85:
81:
77:
73:
69:
65:
57:
54:containing a
53:
49:
45:
41:
32:
19:
2305:
2298:
2212:Vinyl halide
2169:
2099:Borinic acid
2094:Boronic acid
2071:Thioxanthate
2025:
1411:Hydrocarbons
1353:
1349:
1343:
1326:
1322:
1316:
1289:
1283:
1266:
1262:
1256:
1231:
1227:
1221:
1207:cite journal
1190:
1186:
1180:
1170:
1162:
1152:
1127:
1123:
1117:
1100:
1096:
1090:
1065:
1061:
1055:
1038:
1032:
1014:
1007:
990:
986:
980:
953:
949:
943:
926:
922:
916:
889:
883:
858:
854:
848:
813:
809:
796:
779:
775:
769:
751:
747:
733:
716:
712:
698:
671:
665:
631:(11): 4–15.
628:
624:
600:
586:
574:esomeprazole
571:
568:
547:Esomeprazole
525:
519:
515:
500:
476:antioxidants
473:
429:
392:
361:
327:
294:
279:2 ArH + SO
262:
246:
207:
197:racemization
193:stereocenter
177:VSEPR theory
166:
119:between the
117:
114:(bipy)·DMSO.
55:
47:
43:
37:
2276:Thiocyanate
2271:Sulfonamide
2236:Perchlorate
2224:Acyl halide
2185:Fluoroethyl
2066:Thionoester
1954:Phosphonium
1939:Phosphinate
1934:Phosphonous
1922:Phosphonate
1621:Hydroperoxy
1443:Cyclopropyl
713:Tetrahedron
582:armodafinil
411:nucleophile
204:Preparation
133:double bond
129:dative bond
76:derivatives
2346:Sulfoxides
2335:Categories
2180:Haloalkane
2051:Thioketone
2006:Persulfide
1902:Phosphorus
1867:Isocyanate
1857:Isonitrile
1758:or oxygen
1756:hydrogen,
1752:not being
1733:Orthoester
1626:Dioxiranes
1604:Enol ether
1492:1-Propenyl
831:10092/2052
657:References
592:methionine
578:omeprazole
559:omeprazole
466:SOH + CH
311:, or NaClO
48:sulphoxide
18:Sulfoxides
2313:inorganic
2147:Tellurium
2061:Thioester
2026:Sulfoxide
2011:Disulfide
1999:Sulfonium
1949:Phosphine
1927:Phosphite
1910:Phosphate
1842:Carbamate
1817:Hydrazone
1750:element,
1748:Only one
1721:Anhydride
1460:Methylene
1144:102494853
1130:: 67–92.
754:: 12–20.
436:mechanism
319:Reactions
303:, Bi(OTf)
242:prochiral
210:oxidation
169:lone pair
151:Chirality
44:sulfoxide
2294:See also
2229:Chloride
2155:Tellurol
2109:Selenium
2076:Xanthate
1790:Ammonium
1772:Nitrogen
1754:carbon,
1711:Carboxyl
1678:Aldehyde
1666:Acryloyl
1648:carbonyl
1552:hydrogen
1507:Cumulene
1248:11749600
1082:96348273
1024:52-12057
875:12964880
840:98211634
565:version.
553:, is an
522:-bonded.
462:R → CH
386:Na + H
287:SO + H
214:sulfides
80:sulfides
56:sulfinyl
50:, is an
2318:organic
2117:Selenol
2041:Sulfone
1994:Sulfide
1892:NONOate
1887:Nitroso
1877:Nitrite
1872:Nitrate
1862:Cyanate
1852:Nitrile
1837:Amidine
1832:Imidate
1802:Nitrene
1797:Hydrazo
1785:Enamine
1716:Acetoxy
1704:carboxy
1671:Benzoyl
1609:Epoxide
1592:Methoxy
1582:Alcohol
1536:Carbene
1470:Methine
1039:Synlett
625:Arkivoc
563:racemic
561:is the
440:alkenes
407:acetate
393:In the
307:, LiClO
226:sulfone
145:dipolar
110:of PdBr
92:solvent
2217:Iodide
2137:Selone
1981:Sulfur
1690:Ketone
1683:Ketene
1661:Acetyl
1616:Peroxy
1587:Alkoxy
1577:Acetal
1558:oxygen
1547:carbon
1531:Alkyne
1524:Benzyl
1519:Phenyl
1502:Allene
1497:Crotyl
1477:Alkene
1465:Bridge
1453:Pentyl
1438:Propyl
1428:Methyl
1304:
1246:
1193:: 29.
1142:
1080:
1022:
968:
929:: 78.
904:
873:
838:
686:
607:ajoene
603:alliin
509:(dmso)
454:S(O)CH
382:S(O)CH
374:S(O)CH
343:
187:. The
125:oxygen
121:sulfur
84:alliin
68:carbon
60:>SO
2249:Other
2086:Boron
2056:Thial
1989:Thiol
1882:Nitro
1847:Imide
1827:Amide
1812:Oxime
1807:Imine
1780:Amine
1728:Ester
1695:Ynone
1599:Ether
1570:R-O-R
1545:Only
1487:Allyl
1482:Vinyl
1448:Butyl
1433:Ethyl
1423:Alkyl
1140:S2CID
1078:S2CID
836:S2CID
806:(PDF)
746:SO".
399:alkyl
283:→ Ar
72:polar
2171:Halo
1656:Acyl
1556:and
1514:Aryl
1302:ISBN
1244:PMID
1213:link
1020:LCCN
966:ISBN
902:ISBN
871:PMID
684:ISBN
629:2003
605:and
549:, a
505:RuCl
470:=CHR
442:and
349:+ H
341:+ 2
337:OSMe
265:aryl
255:.
123:and
42:, a
1822:Azo
1358:doi
1354:248
1331:doi
1294:doi
1271:doi
1236:doi
1195:doi
1132:doi
1128:284
1105:doi
1070:doi
1043:doi
995:doi
958:doi
931:doi
894:doi
863:doi
859:103
826:hdl
818:doi
784:doi
756:doi
721:doi
676:doi
643:hdl
633:doi
501:cis
446:.
212:of
78:of
38:In
2337::
1554:,
1549:,
1352:.
1327:11
1325:.
1300:.
1292:.
1267:91
1265:.
1242:.
1232:66
1230:.
1209:}}
1205:{{
1191:70
1189:.
1168:;
1161:.
1138:.
1126:.
1101:43
1099:.
1076:.
1066:34
1064:.
991:88
989:.
964:.
956:.
927:46
925:.
900:.
869:.
857:.
834:.
824:.
814:80
812:.
808:.
780:93
778:.
752:21
750:.
742:C)
717:67
715:.
707:CO
682:.
641:.
627:.
623:.
609:.
584:.
458:CH
450:CH
413::
397:,
370:CH
366::
315:.
220:.
167:A
94:.
62:)
1395:e
1388:t
1381:v
1364:.
1360::
1337:.
1333::
1310:.
1296::
1277:.
1273::
1250:.
1238::
1215:)
1201:.
1197::
1175:.
1146:.
1134::
1111:.
1107::
1084:.
1072::
1049:.
1045::
1026:.
1001:.
997::
974:.
960::
950:R
937:.
933::
910:.
896::
877:.
865::
842:.
828::
820::
790:.
786::
764:.
762:.
758::
744:2
740:3
727:.
723::
709:3
705:2
692:.
678::
651:.
645::
635::
520:O
516:S
511:4
507:2
503:-
468:2
464:3
460:2
456:2
452:3
434:i
432:E
388:2
384:2
380:3
376:3
372:3
353:O
351:2
347:2
339:2
313:4
309:4
305:3
301:3
291:O
289:2
285:2
281:2
163:.
112:2
58:(
20:)
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