190:
28:
37:
521:
532:
The behavior of the secondary phospholes, those with P−H bond, is dominated by the reactivity of this group. The parent phosphole readily rearranges by migration of H from P to carbon-2, followed by dimerization.
483:
of phosphorus. The absence of aromaticity is also indicated by the reactivity of phospholes. Phospholes undergo different cycloaddition reactions; coordination properties of phospholes are also well studied.
536:
Most phospholes are tertiary, typically P-methyl or P-phenyl. The nonaromaticity of these phospholes is manifested in their reactivity but the P−C bonds remain intact. For example, they undergo
492:
The parent phosphole was first described in 1983. It was prepared by low-temperature protonation of lithium phospholide. Pentaphenylphosphole was reported in 1953. One route to phospholes is via the
752:
Claude
Charrier; Hubert Bonnard; Guillaume De Lauzon; Francois Mathey (1983). "Proton shifts in P-unsubstituted 1H-phospholes. Synthesis and chemistry of 2H-phosphole dimers".
550:
2,5-Diphenyl phospholes can be functionalised by deprotonation followed by P-acylation then a 1H, 2H, 3H phospholide equilibrium resulting in a 1:3 shift of the acyl group.
945:
226:
1380:
650:
938:
790:
204:
1370:
858:
Magali
Clochard; Joanna Grundy; Bruno Donnadieu & François Mathey (2005). "A straightforward synthesis of 3-acylphospholes".
931:
328:
1375:
168:
634:
693:
Philip
Hindenberg; Carlos Romero-Nieto (2016). "Phosphaphenalenes: An Evolution of the Phosphorus Heterocycles".
584:
389:
537:
893:
Grundy, J. & Mathey, F. (2005). "One-Pot
Conversion of Phospholide Ions into β-Functional Phosphinines".
666:
D. B. Chesnut; L. D. Quin (2007). "The important role of the phosphorus lone pair in phosphole aromaticity".
509:
381:
1165:
954:
55:
185:
1283:
505:
77:
562:
493:
111:
1243:
910:
875:
836:
808:
786:
646:
720:
Almaz
Zagidullin; Vasily A. Miluykov (2013). "Phospholes – development and recent advances".
631:
Nomenclature of
Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book)
1202:
902:
867:
761:
729:
702:
675:
638:
558:
480:
348:
344:
249:
131:
1197:
520:
87:
189:
1248:
1238:
1192:
980:
574:
472:
322:
27:
36:
1364:
1278:
1273:
1253:
1223:
1309:
541:
156:
553:
Phospholes can also be turned into β-functional phosphabenzenes (phosphinines, or
733:
1329:
1319:
1314:
1299:
1268:
1041:
831:
803:
642:
589:
554:
508:. Phenylphospholes can be prepared via zirconacyclopentadienes by reaction with
313:
1218:
1092:
1087:
373:
274:
122:
1324:
1304:
1233:
1107:
1102:
1056:
1051:
1031:
1011:
1006:
579:
476:
460:
914:
906:
879:
706:
380:. The term phosphole also refers to substituted derivatives of the parent
1263:
1112:
1097:
1082:
1077:
1046:
1036:
1021:
975:
468:
923:
765:
471:
of phospholes is diminished, reflecting the reluctance of phosphorus to
1345:
1149:
1133:
1128:
1072:
1026:
1001:
456:
377:
309:
301:
297:
143:
871:
1258:
1228:
679:
544:
385:
305:
321:
Except where otherwise noted, data are given for materials in their
996:
497:
464:
110:
100:
384:. These compounds are of theoretical interest but also serve as
927:
173:
35:
26:
388:
for transition metals and as precursors to more complex
1338:
1292:
1211:
1185:
1178:
1158:
1142:
1121:
1065:
989:
968:
961:
479:. The main indication of this difference is the
447:, is a cyclic compound with 5 phosphorus atoms.
155:
86:
939:
8:
428:, is a heterocycle with 3 phosphorus atoms.
547:. They are basic at P, serving as ligands.
455:Unlike the related 5-membered heterocycles
1182:
965:
946:
932:
924:
188:
130:
15:
830:Paul J. Fagan; William A. Nugent (1998).
747:
745:
743:
895:Angewandte Chemie International Edition
832:"1-Phenyl-2,3,4,5-Tetramethylphosphole"
622:
231:
209:
184:
779:A Guide to Organophosphorus Chemistry
7:
804:"3-Methyl-1-Phenylphospholene oxide"
146:
1381:Substances discovered in the 1980s
496:, involving the addition of a 1,3-
267:
14:
213:InChI=1S/C4H5P/c1-2-4-5-3-1/h1-5H
519:
261:
500:to a phosphonous chloride (RPCl
325:(at 25 °C , 100 kPa).
635:The Royal Society of Chemistry
255:
1:
734:10.1016/j.mencom.2013.05.001
643:10.1039/9781849733069-00130
557:) via functionalisation by
22:
1397:
846:, vol. 9, p. 653
818:, vol. 5, p. 787
390:organophosphorus compounds
585:Organophosphorus compound
319:
286:
242:
222:
200:
70:
54:
49:
21:
802:W. B. McCormack (1973).
722:Mendeleev Communications
1371:Phosphorus heterocycles
907:10.1002/anie.200462020
785:John Wiley & Sons
707:10.1055/s-0035-1562506
40:
31:
955:Simple aromatic rings
637:. 2014. p. 146.
538:Diels–Alder reactions
451:Structure and bonding
39:
30:
1166:Cyclooctadecanonaene
668:Heteroatom Chemistry
56:Preferred IUPAC name
1376:Five-membered rings
1284:5-Aza-7-deazapurine
766:10.1021/ja00361a022
506:dehydrohalogenation
282: g·mol
18:
494:McCormack reaction
329:Infobox references
287:Related compounds
41:
32:
16:
1358:
1357:
1354:
1353:
1244:Benzo(c)thiophene
1174:
1173:
872:10.1021/ol051816d
866:(20): 4511–4513.
844:Collected Volumes
837:Organic Syntheses
816:Collected Volumes
809:Organic Syntheses
652:978-0-85404-182-4
337:Chemical compound
335:
334:
293:Related compounds
169:CompTox Dashboard
112:Interactive image
45:
44:
1388:
1203:Trithiapentalene
1183:
966:
948:
941:
934:
925:
919:
918:
890:
884:
883:
855:
849:
847:
840:
827:
821:
819:
812:
799:
793:
776:
770:
769:
754:J. Am. Chem. Soc
749:
738:
737:
717:
711:
710:
690:
684:
683:
680:10.1002/hc.20364
663:
657:
656:
627:
613:
611:
610:
602:
601:
559:imidoyl chloride
523:
481:pyramidalization
446:
444:
443:
427:
426:
425:
417:
416:
408:
407:
371:
369:
368:
360:
359:
349:chemical formula
345:organic compound
281:
269:
263:
257:
250:Chemical formula
193:
192:
177:
175:
159:
148:
134:
114:
90:
23:
19:
1396:
1395:
1391:
1390:
1389:
1387:
1386:
1385:
1361:
1360:
1359:
1350:
1334:
1288:
1207:
1198:Thienothiophene
1170:
1154:
1138:
1117:
1061:
985:
957:
952:
922:
892:
891:
887:
860:Organic Letters
857:
856:
852:
842:
829:
828:
824:
814:
801:
800:
796:
777:
773:
751:
750:
741:
719:
718:
714:
692:
691:
687:
665:
664:
660:
653:
629:
628:
624:
620:
609:
606:
605:
604:
600:
597:
596:
595:
593:
571:
530:
513:
503:
490:
453:
442:
439:
438:
437:
435:
424:
421:
420:
419:
415:
412:
411:
410:
406:
403:
402:
401:
399:
367:
364:
363:
362:
358:
355:
354:
353:
351:
338:
331:
326:
294:
279:
266:
260:
252:
238:
235:
230:
229:
218:
215:
214:
208:
207:
196:
178:
171:
162:
149:
137:
117:
104:
93:
80:
66:
65:
12:
11:
5:
1394:
1392:
1384:
1383:
1378:
1373:
1363:
1362:
1356:
1355:
1352:
1351:
1349:
1348:
1342:
1340:
1336:
1335:
1333:
1332:
1327:
1322:
1317:
1312:
1307:
1302:
1296:
1294:
1290:
1289:
1287:
1286:
1281:
1276:
1271:
1266:
1261:
1256:
1251:
1249:Benzophosphole
1246:
1241:
1239:Benzothiophene
1236:
1231:
1226:
1221:
1215:
1213:
1209:
1208:
1206:
1205:
1200:
1195:
1193:Diazapentalene
1189:
1187:
1180:
1176:
1175:
1172:
1171:
1169:
1168:
1162:
1160:
1156:
1155:
1153:
1152:
1146:
1144:
1140:
1139:
1137:
1136:
1131:
1125:
1123:
1122:Seven-membered
1119:
1118:
1116:
1115:
1110:
1105:
1100:
1095:
1090:
1085:
1080:
1075:
1069:
1067:
1063:
1062:
1060:
1059:
1054:
1049:
1044:
1039:
1034:
1029:
1024:
1019:
1014:
1009:
1004:
999:
993:
991:
987:
986:
984:
983:
981:Cyclopropenone
978:
972:
970:
969:Three-membered
963:
959:
958:
953:
951:
950:
943:
936:
928:
921:
920:
885:
850:
822:
794:
781:Louis D. Quin
771:
739:
712:
685:
658:
651:
621:
619:
616:
615:
614:
607:
598:
587:
582:
577:
575:Benzophosphole
570:
567:
529:
526:
525:
524:
511:
504:) followed by
501:
489:
486:
452:
449:
440:
432:Pentaphosphole
422:
413:
404:
365:
356:
336:
333:
332:
327:
323:standard state
320:
317:
316:
295:
292:
289:
288:
284:
283:
277:
271:
270:
264:
258:
253:
248:
245:
244:
240:
239:
237:
236:
233:
225:
224:
223:
220:
219:
217:
216:
212:
211:
203:
202:
201:
198:
197:
195:
194:
186:DTXSID60182977
181:
179:
167:
164:
163:
161:
160:
152:
150:
142:
139:
138:
136:
135:
127:
125:
119:
118:
116:
115:
107:
105:
98:
95:
94:
92:
91:
83:
81:
76:
73:
72:
68:
67:
59:
58:
52:
51:
47:
46:
43:
42:
33:
13:
10:
9:
6:
4:
3:
2:
1393:
1382:
1379:
1377:
1374:
1372:
1369:
1368:
1366:
1347:
1344:
1343:
1341:
1337:
1331:
1328:
1326:
1323:
1321:
1318:
1316:
1313:
1311:
1308:
1306:
1303:
1301:
1298:
1297:
1295:
1291:
1285:
1282:
1280:
1279:Benzothiazole
1277:
1275:
1274:Benzisoxazole
1272:
1270:
1267:
1265:
1262:
1260:
1257:
1255:
1254:Benzimidazole
1252:
1250:
1247:
1245:
1242:
1240:
1237:
1235:
1232:
1230:
1227:
1225:
1224:Isobenzofuran
1222:
1220:
1217:
1216:
1214:
1210:
1204:
1201:
1199:
1196:
1194:
1191:
1190:
1188:
1184:
1181:
1177:
1167:
1164:
1163:
1161:
1157:
1151:
1148:
1147:
1145:
1143:Nine-membered
1141:
1135:
1132:
1130:
1127:
1126:
1124:
1120:
1114:
1111:
1109:
1106:
1104:
1101:
1099:
1096:
1094:
1091:
1089:
1086:
1084:
1081:
1079:
1076:
1074:
1071:
1070:
1068:
1064:
1058:
1055:
1053:
1050:
1048:
1045:
1043:
1040:
1038:
1035:
1033:
1030:
1028:
1025:
1023:
1020:
1018:
1015:
1013:
1010:
1008:
1005:
1003:
1000:
998:
995:
994:
992:
990:Five-membered
988:
982:
979:
977:
974:
973:
971:
967:
964:
960:
956:
949:
944:
942:
937:
935:
930:
929:
926:
916:
912:
908:
904:
901:: 1082–1084.
900:
896:
889:
886:
881:
877:
873:
869:
865:
861:
854:
851:
845:
839:
838:
833:
826:
823:
817:
811:
810:
805:
798:
795:
792:
791:0-471-31824-8
788:
784:
780:
775:
772:
767:
763:
760:: 6871–6877.
759:
755:
748:
746:
744:
740:
735:
731:
727:
723:
716:
713:
708:
704:
701:: 2293–2300.
700:
696:
689:
686:
681:
677:
673:
669:
662:
659:
654:
648:
644:
640:
636:
633:. Cambridge:
632:
626:
623:
617:
591:
588:
586:
583:
581:
578:
576:
573:
572:
568:
566:
564:
560:
556:
551:
548:
546:
543:
542:electrophilic
539:
534:
527:
522:
518:
517:
516:
514:
507:
499:
495:
487:
485:
482:
478:
474:
470:
466:
462:
458:
450:
448:
433:
429:
397:
393:
391:
387:
383:
379:
375:
350:
346:
342:
330:
324:
318:
315:
311:
307:
303:
299:
296:
291:
290:
285:
278:
276:
273:
272:
254:
251:
247:
246:
241:
232:
228:
221:
210:
206:
199:
191:
187:
183:
182:
180:
170:
166:
165:
158:
154:
153:
151:
145:
141:
140:
133:
129:
128:
126:
124:
121:
120:
113:
109:
108:
106:
102:
97:
96:
89:
85:
84:
82:
79:
75:
74:
69:
63:
57:
53:
48:
38:
34:
29:
25:
24:
20:
1339:Five + Seven
1310:Isoquinoline
1066:Six-membered
1016:
898:
894:
888:
863:
859:
853:
843:
835:
825:
815:
807:
797:
782:
778:
774:
757:
753:
725:
721:
715:
698:
694:
688:
671:
667:
661:
630:
625:
552:
549:
535:
531:
491:
454:
431:
430:
396:Triphosphole
395:
394:
372:; it is the
340:
339:
71:Identifiers
61:
1330:Phthalazine
1320:Quinazoline
1315:Quinoxaline
1300:Naphthalene
1269:Benzoxazole
1186:Five + Five
1159:18-membered
1042:Isothiazole
728:: 117–130.
590:Phosphorine
555:phosphorine
488:Preparation
469:aromaticity
382:heterocycle
314:phosphorine
243:Properties
1365:Categories
1219:Benzofuran
1212:Five + Six
1093:Pyridazine
1088:Pyrimidine
618:References
528:Reactivity
473:delocalize
376:analog of
374:phosphorus
275:Molar mass
123:ChemSpider
99:3D model (
78:CAS Number
64:-Phosphole
17:Phosphole
1325:Cinnoline
1305:Quinoline
1293:Six + Six
1234:Isoindole
1108:Pentazine
1103:Tetrazine
1057:Pentazole
1052:Tetrazole
1032:Isoxazole
1017:Phosphole
1012:Thiophene
1007:Imidazole
580:Metallole
563:insertion
477:lone pair
461:thiophene
347:with the
341:Phosphole
234:P1C=CC=C1
1264:Indazole
1113:Hexazine
1098:Triazine
1083:Pyrazine
1078:Pyridine
1047:Triazole
1037:Thiazole
1022:Pyrazole
976:Borirene
915:15662672
880:16178571
569:See also
88:288-01-7
1346:Azulene
1179:2 rings
1150:Azonine
1134:Tropone
1129:Borepin
1073:Benzene
1027:Oxazole
1002:Pyrrole
695:Synlett
674:: 754.
545:alkynes
457:pyrrole
386:ligands
378:pyrrole
343:is the
310:stibole
302:bismole
298:Pyrrole
144:PubChem
1259:Purine
1229:Indole
962:1 ring
913:
878:
789:
649:
467:, the
463:, and
306:arsole
280:84.058
227:SMILES
157:164575
132:144273
50:Names
997:Furan
540:with
510:PhPCl
498:diene
465:furan
205:InChI
101:JSmol
911:PMID
876:PMID
787:ISBN
783:2000
647:ISBN
561:and
475:its
903:doi
868:doi
762:doi
758:105
730:doi
703:doi
676:doi
639:doi
174:EPA
147:CID
1367::
909:.
899:44
897:.
874:.
862:.
841:;
834:.
813:;
806:.
756:.
742:^
726:23
724:.
699:27
697:.
672:18
670:.
645:.
592:,
565:.
515:.
459:,
434:,
398:,
392:.
370:PH
312:;
308:,
304:,
300:,
947:e
940:t
933:v
917:.
905::
882:.
870::
864:7
848:.
820:.
768:.
764::
736:.
732::
709:.
705::
682:.
678::
655:.
641::
612:P
608:5
603:H
599:5
594:C
512:2
502:2
445:H
441:5
436:P
423:3
418:P
414:3
409:H
405:2
400:C
366:4
361:H
357:4
352:C
268:P
265:5
262:H
259:4
256:C
176:)
172:(
103:)
62:H
60:1
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