RADICAL CYCLIZATIONS OF FUNCTIONALIZED ALLENES

被引:25
作者
CRANDALL, JK
AYERS, TA
机构
[1] Department of Chemistry, Indiana University, Bloomington
关键词
ALLENE; RADICAL CYCLIZATION; SULFONE; PHOSPHINE OXIDE;
D O I
10.1016/S0040-4039(00)79759-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Substitution of P(O)Ph2, SOPh and SO2Ph on an allene facilitates intramolecular radical addition to the central allene carbon to provide good yields of five-, six-, and seven-membered carbocycles.
引用
收藏
页码:3659 / 3662
页数:4
相关论文
共 32 条
[1]   CYCLIZATIONS OF OMEGA-ALLENYL RADICALS [J].
APPARU, M ;
CRANDALL, JK .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (12) :2125-2130
[2]  
ARSENIYADIS S, 1978, J CHEM RES-S, P416
[3]   FROM ALLENIC PHOSPHORUS DERIVATIVES TO HETEROCYCLIC-COMPOUNDS - SYNTHESIS OF A 1,2,3-DIAZAPHOSPHOLE COMPOUND WITH A STRONGLY POLAR NH GROUP LINKED TO A DICOORDINATE PHOSPHORUS ATOM [J].
AYED, N ;
BACCAR, B ;
MATHIS, F ;
MATHIS, R .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1985, 21 (03) :335-347
[4]   FREE-RADICAL ANNELATION IN THE SYNTHESIS OF BICYCLIC BETA-LACTAMS .4. EXO VS ENDO CYCLIZATIONS IN THE CONSTRUCTION OF THE (+/-)-1-OXACEPHAM AND (+/-)-1-OXAHOMOCEPHAM SYSTEMS [J].
BACHI, MD ;
FROLOW, F ;
HOORNAERT, C .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (11) :1841-1849
[5]   MULTIPLE RADICAL ADDITIONS - AN EXPEDIENT ENTRY INTO COMPLEX FRAMEWORKS [J].
BARTON, DHR ;
DASILVA, E ;
ZARD, SZ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (04) :285-287
[6]  
Beckwith A. L. J., 1980, REARRANGEMENTS GROUN, V1, P162
[7]   REGIO-SELECTIVITY AND STEREO-SELECTIVITY OF ALKENYL RADICAL RING-CLOSURE - A THEORETICAL-STUDY [J].
BECKWITH, ALJ ;
SCHIESSER, CH .
TETRAHEDRON, 1985, 41 (19) :3925-3941
[8]   ACETYLENE-ALLENE REARRANGEMENTS - REACTIONS OF TRIVALENT PHOSPHORUS CHLORIDES WITH ALPHA-ACETYLENIC ALCOHOLS AND GLYCOLS [J].
BOISSELLE, AP ;
MEINHARDT, NA .
JOURNAL OF ORGANIC CHEMISTRY, 1962, 27 (05) :1828-&
[9]   PYRROLIZIDINONE AND INDOLIZIDINONE SYNTHESIS - GENERATION AND INTRAMOLECULAR ADDITION OF ALPHA-ACYLAMINO RADICALS TO OLEFINS AND ALLENES [J].
BURNETT, DA ;
CHOI, JK ;
HART, DJ ;
TSAI, YM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (26) :8201-8209
[10]   REDUCTIVE CYCLIZATIONS OF ALLENIC KETONES BY DISSOLVING METALS [J].
CRANDALL, JK ;
MUALLA, M .
TETRAHEDRON LETTERS, 1986, 27 (20) :2243-2246