562:
469:
608:
208:
457:
709:
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688:
24:
628:
45:
476:
It is sometimes incorrectly claimed that Dewar proposed his structure as the true structure of benzene. In fact, Dewar merely wrote the structure as one of seven possible isomers and believed that his experiments on benzene supported the (correct) structure that had been proposed by
1498:
Junker, Hans-Nikolaus; Schäfer, Wolfgang; Niedenbrück, Hans (1967). "Oxydationsreaktionen mit
Hexamethyl-bicyclo-hexadien-(2.5) (= Hexamethyl-Dewar-Benzol)" [Oxidation reactions with hexamethylbicyclo-hexa-2,5-diene (= Hexamethyl Dewar Benzene)].
561:
492:
contributors, the two Kekulé structures. The three possible Dewar structures were considered as minor resonance contributors in the overall description of benzene, alongside other classic structures such as the isomers
1659:; Krow, Grant R.; Bollinger, J. Martin; Olah, George A. (1968). "Protonation of hexamethyl Dewar benzene and hexamethylprismane in fluorosulfuric acid – antimony pentafluoride – sulfur dioxide".
1947:
558:
results in the formation of a pentamethylcyclopentadiene complex, , indicating that the rhodium and iridium metal centres are necessary for the step in which the aromatic anion is formed.
1531:
Asouti, Amalia; Hadjiarapoglou, Lazaros P. (2000). "Regioselective and diastereoselective dimethyldioxirane epoxidation of substituted norbornenes and hexamethyl Dewar benzene".
544:
540:
776:
of about 0.54; it follows that the total bond order for the apical carbon is 5 × 0.54 + 1 = 3.7 < 4, and thus the species is not
1919:
257:
2049:
772:
discussed the dication, noting that the weak bonds forming the upright edges of the pyramid, shown as dashed lines in the structure he drew, have a Wiberg
456:
383:
Unlike benzene, Dewar benzene is not flat because the carbons where the rings join are bonded to four atoms rather than three. These carbons tend toward
371:
structures in 1869. However, he did not propose it as the structure of benzene, and in fact he supported the correct structure previously proposed by
2011:
478:
957:
1984:
1937:
854:, commented that one the motivations for undertaking the work was to illustrate "the possibility to astonish chemists about what can be possible."
1428:
Synthetic
Methods of Organometallic and Inorganic Chemistry – Volume 1: Literature, Laboratory Techniques, and Common Starting Materials
1247:
Synthetic
Methods of Organometallic and Inorganic Chemistry – Volume 1: Literature, Laboratory Techniques, and Common Starting Materials
850:, and ZME Science, the structure is consistent with the usual bonding rules of chemistry. Moritz Malischewski, who carried out the work with
680:. The pyramidal structure having an apex carbon bonding to six other carbon atoms was confirmed by X-ray crystallographic analysis of the
780:, but it is hypercoordinate. From the perspective of organometallic chemistry, the species can be viewed as having a carbon(IV) centre (
1888:
1439:
1297:
1258:
879:"On the Oxidation af Phenyl Alcohol, and a Mechanical Arrangement adapted to illustrate Structure in the Non-saturated Hydrocarbons"
468:
222:
672:, which removes the oxygen as an anion. NMR had previously hinted at a pentagonal pyramidal structure in a related cation as had
1800:
Hogeveen, Hepke; Kwant, Peter W. (1975). "Pyramidal mono- and dications. Bridge between organic and organometallic chemistry".
668:, was produced by Hepke Hogeveen and Peter Kwant. This can be done by dissolving the hexamethyl Dewar benzene monoepoxide in
555:
834:
1056:; Pappas, S. P.; Kirk, K. L. (1971). "Valence Bond Isomers of Aromatic Systems. Bicyclohexa-2,5-dienes (Dewar benzenes)".
1687:
Hogeveen, Hepke; Kwant, Peter W.; Postma, J.; van Duynen, P. Th. (1974). "Electronic spectra of pyramidal dications, (CCH
317:
165:
1559:
Hogeveen, Hepke; Kwant, Peter W. (1973). "Direct observation of a remarkably stable dication of unusual structure: (CCH
604:
CPBA or peroxybenzoic acid), the epoxy product quickly rearranges, catalyzed by the acid byproduct of the epoxidation.
797:
186:
699:
548:
607:
109:
1778:
1831:; Samdal, Svein; Seip, Ragnhild (1978). "The molecular structure of monomeric methyl(cyclopentadienyl)zinc, (CH
537:
389:
551:
1999:
1727:
Hogeveen, Hepke; Kwant, Peter W. (1974). "Chemistry and spectroscopy in strongly acidic solutions. XL. (CCH
1197:; Grüner, H. (1968). "Acid-catalyzed Rearrangements of Hexamethyl-prismane and Hexamethyl-Dewar-benzene".
525:
424:
2044:
2039:
1970:
1622:
1199:
1089:
489:
1905:
1880:
1378:(1968). "Conversion of Dewar Hexamethylbenzene to Pentamethylcyclopentadienylrhodium(III) Chloride".
925:
883:
777:
681:
505:. Prismane and benzvalene were synthesized in the 1970s; Claus' benzene is impossible to synthesize.
384:
57:
618:. By varying the amount of DMDO, either the mono- or diepoxide can be formed, with the oxygen atoms
203:
1845:
1431:
1250:
806:
485:
75:
1227:"Bis{(μ-chloro)[chloro(η-pentamethylcyclopentadienyl)rhodium]} — {Rh(μ-Cl)Cl[η-C
2007:
1608:(2016). "Crystal Structure Determination of the Pentagonal-Pyramidal Hexamethylbenzene Dication C
1349:(1968). "Mechanisms of Reactions of Dewar Hexamethylbenzene with Rhodium and Iridium Chlorides".
1053:
1022:
984:
620:
589:
521:
440:
428:
406:
402:
1317:(1969). "Pentamethylcyclopentadienylrhodium and -iridium halides. I. Synthesis and properties".
627:
1884:
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993:
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448:
1872:
878:
614:
Using DMDO gives the epoxide as a stable product—the byproduct of the epoxidation is neutral
1853:
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anion (six-electron donor) and a methyl anion (two-electron donor), thereby satisfying the
174:
129:
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529:
85:
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23:
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44:
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1942:
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1314:
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398:
472:
Seven possible isomers proposed by Dewar, with "Dewar benzene" in second row, right.
1975:
1828:
1656:
1163:
970:
912:
846:
673:
34:
547:
dimers; consequently, it can be used as a starting material for synthesising some
154:
1459:
1124:
874:
578:
394:
360:
30:
1501:
1166:; Krow, Grant R. (1968). "Electrophilic Additions to Hexamethyldewarbenzene".
895:
802:
773:
669:
498:
432:
418:
299:
120:
1514:
1477:
1142:
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793:
444:
1642:
1634:
1282:"Reactions of Dienes Trienes and Tetraenes with Transition Metal Compounds"
1211:
1109:
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832:
on the metal. Thus, while unprecedented, and having attracted comment in
1360:
759:
677:
494:
341:
1814:
1749:
1673:
1392:
1331:
1070:
1039:
1005:
953:"Vibrational Frequencies and Structural Determination of Dewar Benzene"
615:
597:
348:
141:
937:
762:'s rearranged pentagonal-pyramid framework, from the crystal structure
560:
405:
of two days. This thermal conversion is relatively slow because it is
814:
574:
344:
2000:"Exotic carbon molecule has six bonds, breaking the four-bond limit"
1408:"Dicarbonyl(η-pentamethylcyclopentadienyl)rhodium — Rh[η-C
952:
310:
Except where otherwise noted, data are given for materials in their
582:
467:
108:
98:
1087:; Hopf, Henning (2008). "Learning from Molecules in Distress".
987:; Pappas, S. P. (1962). "Chemistry of Dewar Benzene. 1,2,5-Tri-
915:; Rouvray, Dennis H. (1978). "Para-Bond or "Dewar" Benzene?".
1938:"Carbon seen bonding with six other atoms for the first time"
488:
in 1928, benzene was described primarily using its two major
387:, and the two cyclobutene rings make an angle where they are
686:
626:
606:
191:
1017:
1015:
397:
to each other. The compound has nevertheless considerable
1286:
Organotransition Metal
Chemistry: A Mechanistic Approach
417:
The compound itself was first synthesized in 1962 as a
1426:. In Herrmann, Wolfgang A.; Salzer, Albrecht (eds.).
1245:. In Herrmann, Wolfgang A.; Salzer, Albrecht (eds.).
363:
who included this structure in a list of possible C
1931:
1929:
1843:), determined by gas phase electron diffraction".
1526:
1524:
1025:; Pappas, S. P. (1963). "Bicyclo hexa-2,5-diene".
1406:Herrmann, Wolfgang A.; Zybill, Christian (1996).
1225:Herrmann, Wolfgang A.; Zybill, Christian (1996).
1458:King, R. B.; Douglas, W. M.; Efraty, A. (1977).
1453:
1451:
554:including . Attempting a similar reaction with
153:
1460:"5-Acetyl-1,2,3,4,5-pentamethylcyclopentadiene"
84:
545:pentamethylcyclopentadienyl iridium dichloride
541:pentamethylcyclopentadienyl rhodium dichloride
1873:"Organometallic Compounds of Groups 2 and 12"
516:has been prepared by bicyclotrimerization of
8:
1761:
1759:
758:: Three-dimensional representation of the
427:and then as the unsubstituted compound by
206:
128:
15:
173:
1904:Ritter, Stephen K. (December 19, 2016).
1123:Shama, Sami A.; Wamser, Carl C. (1990).
1272:
1270:
907:
905:
869:
867:
863:
262:
227:
202:
1987:from the original on February 3, 2017.
1599:
1597:
1595:
1593:
1591:
2014:from the original on January 16, 2017
1950:from the original on January 16, 2017
1922:from the original on January 9, 2017.
1781:from the original on January 19, 2017
805:and being analogous to the gas-phase
409:based on orbital symmetry arguments.
234:Key: CTLSARLLLBZBRV-UHFFFAOYSA-N
7:
1969:Hamers, Laurel (December 24, 2016).
565:Synthesis of the rhodium(III) dimer
231:InChI=1S/C6H6/c1-2-6-4-3-5(1)6/h1-6H
1971:"Carbon can exceed four-bond limit"
1936:Boyle, Rebecca (January 14, 2017).
244:Key: CTLSARLLLBZBRV-UHFFFAOYAO
241:InChI=1/C6H6/c1-2-6-4-3-5(1)6/h1-6H
144:
2050:Substances discovered in the 1960s
624:on the bicyclic carbon framework.
14:
1871:Elschenbroich, Christoph (2006).
1906:"Six bonds to carbon: Confirmed"
707:
698:
455:
43:
22:
835:Chemical & Engineering News
314:(at 25 °C , 100 kPa).
33:rings of Dewar benzene form an
1998:Puiu, Tibi (January 5, 2017).
1771:"A six-coordinate carbon atom"
991:-ButylbicycloHexa-2,5-Diene".
971:10.1016/j.theochem.2004.03.042
768:Computational organic chemist
556:potassium tetrachloroplatinate
401:and reverts to benzene with a
359:. The compound is named after
1:
1858:10.1016/S0022-328X(00)85041-X
1714:10.1016/S0040-4039(01)92161-6
1582:10.1016/S0040-4039(01)96023-X
1546:10.1016/S0040-4039(99)02113-9
1181:10.1016/S0040-4039(00)89761-0
636:dication of hexamethylbenzene
569:from hexamethyl Dewar benzene
304:78.1 g·mol
1313:Kang, Jung W.; Moseley, K.;
817:bound to a zinc(II) centre (
351:with the molecular formula C
798:pentamethylcyclopentadienyl
549:pentamethylcyclopentadienyl
464:"Dewar benzene" and benzene
439:-1,2-dihydro derivative of
2066:
1151:, vol. 7, p. 256
1125:"Hexamethyl Dewar Benzene"
676:on the Hogeveen and Kwant
1486:, vol. 6, p. 39
1345:Kang, J. W.; Mosley, K.;
951:Jensen, James O. (2004).
896:10.1017/S0370164600045387
536:can be added to form the
532:to which the appropriate
484:After the development of
308:
273:
253:
218:
68:
56:
51:
42:
21:
1735:, an unusual dication".
1515:10.1002/cber.19671000807
1478:10.15227/orgsyn.056.0001
1143:10.15227/orgsyn.061.0062
958:J. Mol. Struct.:THEOCHEM
684:salt published in 2016.
552:organometallic compounds
514:Hexamethyl Dewar benzene
509:Hexamethyl Dewar benzene
379:Structure and properties
791:) bound to an aromatic
1635:10.1002/anie.201608795
1604:Malischewski, Moritz;
1212:10.1002/anie.196804672
1102:10.1002/anie.200705775
1054:van Tamelen, Eugene E.
1023:van Tamelen, Eugene E.
985:van Tamelen, Eugene E.
691:
631:
611:
570:
526:rearrangement reaction
473:
1881:John Wiley & Sons
1623:Angew. Chem. Int. Ed.
1200:Angew. Chem. Int. Ed.
1090:Angew. Chem. Int. Ed.
690:
630:
610:
564:
471:
338:bicyclohexa-2,5-diene
62:Bicyclohexa-2,5-diene
1769:(January 17, 2017).
1708:(49–50): 4351–4354.
1434:. pp. 147–148.
1361:10.1039/C19680001304
1292:. pp. 116–117.
1253:. pp. 148–149.
884:Proc. R. Soc. Edinb.
828:) and satisfies the
682:hexafluoroantimonate
385:tetrahedral geometry
58:Preferred IUPAC name
1846:J. Organomet. Chem.
1815:10.1021/ar50096a004
1767:Bachrach, Steven M.
1750:10.1021/ja00814a034
1674:10.1021/ja01027a060
1432:Georg Thieme Verlag
1393:10.1021/ja01014a063
1332:10.1021/ja01050a008
1251:Georg Thieme Verlag
1071:10.1021/ja00752a021
1040:10.1021/ja00903a056
1006:10.1021/ja00878a054
930:1978JChEd..55..645B
813:which has the same
486:valence bond theory
18:
1883:. pp. 59–85.
692:
632:
612:
590:peroxybenzoic acid
571:
524:. It undergoes a
522:aluminium chloride
474:
441:phthalic anhydride
429:Eugene van Tamelen
407:symmetry forbidden
403:chemical half-life
318:Infobox references
16:
1738:J. Am. Chem. Soc.
1702:Tetrahedron Lett.
1668:(25): 7147–7149.
1662:J. Am. Chem. Soc.
1576:(19): 1665–1670.
1570:Tetrahedron Lett.
1534:Tetrahedron Lett.
1484:Collected Volumes
1465:Organic Syntheses
1387:(12): 3259–3261.
1381:J. Am. Chem. Soc.
1376:Maitlis, Peter M.
1355:(21): 1304–1305.
1347:Maitlis, Peter M.
1326:(22): 5970–5977.
1320:J. Am. Chem. Soc.
1315:Maitlis, Peter M.
1175:(17): 2139–2142.
1169:Tetrahedron Lett.
1149:Collected Volumes
1130:Organic Syntheses
1096:(24): 4474–4481.
1065:(23): 6092–6101.
1059:J. Am. Chem. Soc.
1034:(20): 3297–3298.
1028:J. Am. Chem. Soc.
1000:(19): 3789–3791.
994:J. Am. Chem. Soc.
938:10.1021/ed055p645
594:dimethyldioxirane
518:dimethylacetylene
449:lead tetraacetate
326:Chemical compound
324:
323:
265:C\1=C\C2/C=C\C/12
187:CompTox Dashboard
110:Interactive image
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1879:(3rd ed.).
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1744:(7): 2208–2214.
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1657:Paquette, Leo A.
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965:(1–3): 227–236.
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830:18 electron rule
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596:(DMDO). Using a
530:hydrohalic acids
459:
281:Chemical formula
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177:
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112:
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1911:Chem. Eng. News
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1803:Acc. Chem. Res.
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1775:comporgchem.com
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720:: Structure of
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2004:zmescience.com
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1852:(2): 187–192.
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1629:(1): 368–370.
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1540:(4): 539–542.
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1290:Academic Press
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1206:(6): 467–468.
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943:
918:J. Chem. Educ.
901:
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852:Konrad Seppelt
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786:
750:, as drawn by
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697:
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662:
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644:
566:
538:organometallic
510:
507:
503:Claus' benzene
465:
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414:
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332:(also spelled
325:
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312:standard state
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69:Identifiers
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2008:ZME Science
1954:January 14,
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1918:(49): 13.
1502:Chem. Ber.
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