Tris(trimethylsilyl)silane as mediator in the radical-based allylation reactions of allyl and 2-functionalized allyl phenyl sulfones

被引:23
作者
Chatgilialoglu, C [1 ]
Alberti, A [1 ]
Ballestri, M [1 ]
Macciantelli, D [1 ]
Curran, DP [1 ]
机构
[1] UNIV PITTSBURGH,DEPT CHEM,PITTSBURGH,PA 15260
基金
美国国家科学基金会; 美国国家卫生研究院;
关键词
D O I
10.1016/0040-4039(96)01355-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Radical allylations with 2-functionalized allyl phenyl sulfones have been performed by using ais(trimethylsilyl)silane as radical mediator. Yields varied from moderate to good depending on the nature of the starting materials. EPR studies on the alkyl radical adducts of allyl sulfones have been performed and conformational information has been obtained for the tert-butyl and tetrahydrofuranyl adducts of 2-carboxy allyl tris(trimethylsilyl)silane. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:6391 / 6394
页数:4
相关论文
共 11 条
[1]  
[Anonymous], 1994, ELECT PARAMAGNETIC R
[2]   INVESTIGATIONS OF STRUCTURE AND CONFORMATION .12. STRUCTURE OF AROMATIC SULFONYL RADICALS - ESR AND INDO MOLECULAR-ORBITAL STUDY [J].
CHATGILIALOGLU, C ;
GILBERT, BC ;
NORMAN, ROC .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1979, (06) :770-775
[3]  
Chatgilialoglu C., 1988, CHEM SULFONES SULFOX, P1081
[4]   NEW REAGENTS FOR RADICAL ALLYLATIONS [J].
CURRAN, DP ;
YOO, BW .
TETRAHEDRON LETTERS, 1992, 33 (46) :6931-6934
[5]   DIRECT FREE-RADICAL SUBSTITUTIONS ON ALLYL AND VINYL HALIDES USING ALKYL-HALIDES HEXABUTYLDITIN [J].
HUVAL, CC ;
SINGLETON, DA .
TETRAHEDRON LETTERS, 1993, 34 (19) :3041-3042
[6]   A NEW-ONE-ELECTRON-CARBON-CARBON BOND FORMING REACTION - SEPARATION OF THE CHAIN PROPAGATION STEPS IN FREE-RADICAL ALLYLATION [J].
KECK, GE ;
BYERS, JH .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (25) :5442-5444
[7]   FREE-RADICAL ADDITION FRAGMENTATION REACTIONS IN SYNTHESIS - A 2ND GENERATION SYNTHESIS OF (+)-PSEUDOMONIC ACID-C [J].
KECK, GE ;
TAFESH, AM .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (25) :5845-5846
[8]   COMPETITION METHODS AND SCALES FOR ALKYL RADICAL REACTION-KINETICS [J].
NEWCOMB, M .
TETRAHEDRON, 1993, 49 (06) :1151-1176
[9]   1,3-REARRANGEMENT OF ALLYLIC SULFONES - REARRANGEMENT-CYCLIZATION OF ALLYLIC 4-PENTENYL SULFONES [J].
PHILLIPS, ED ;
WHITHAM, GH .
TETRAHEDRON LETTERS, 1993, 34 (15) :2537-2540
[10]   New radical allylation reaction [J].
QuicletSire, B ;
Zard, SZ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (05) :1209-1210