AN UNEXPECTED STEREOCHEMICAL CONTROL OF ALKENE FORMATION BY THE CHOICE OF RADICAL INITIATOR - THE REVERSIBLE ADDITION OF (ME3SI)3SI. RADICALS TO ALKENES

被引:13
作者
FERRERI, C
BALLESTRI, M
CHATGILIALOGLU, C
机构
[1] CNR, CEA, I CO, I-40064 OZZANO DELL EMILIA, ITALY
[2] UNIV NAPLES, DIPARTIMENTO CHIM ORGAN & BIOL, I-80134 NAPLES, ITALY
关键词
D O I
10.1016/S0040-4039(00)60699-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Tris(trimethylsilyl)silyl radical is effective in isomerizing some (Z)-olefins into their thermodynamically more stable (E)-isomers by an addition-elimination path.
引用
收藏
页码:5147 / 5150
页数:4
相关论文
共 18 条
[1]  
BENNETT JE, 1971, CHEM PHYS LETT, V9, P460, DOI 10.1016/0009-2614(71)80268-3
[2]   ORGANOSILANES AS RADICAL-BASED REDUCING AGENTS IN SYNTHESIS [J].
CHATGILIALOGLU, C .
ACCOUNTS OF CHEMICAL RESEARCH, 1992, 25 (04) :188-194
[3]  
CURRAN DP, UNPUB COMMUNICATION
[4]   THE STEREOSELECTIVITY OF INTERMOLECULAR FREE-RADICAL REACTIONS [J].
GIESE, B .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1989, 28 (08) :969-980
[5]   INFLUENCE OF H-DONOR AND TEMPERATURE ON THE STEREOSELECTIVITY OF RADICAL REACTIONS [J].
GIESE, B ;
GONZALEZGOMEZ, JA ;
LACHHEIN, S ;
METZGER, JO .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1987, 26 (05) :479-480
[6]   ISOSELECTIVE RELATIONSHIP FOR THE STEREOSELECTIVITY OF THE TRANSFER OF HYDROGEN-ATOMS TO CYCLIC ALKYL RADICALS [J].
GIESE, B ;
FARSHCHI, H ;
HARTMANNS, J ;
METZGER, JO .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1991, 30 (05) :600-601
[7]   DETERMINATION OF ADDITION RATES OF BENZENETHIYL RADICALS TO ALKYNES BY FLASH-PHOTOLYSIS - STRUCTURES OF PRODUCED VINYL-TYPE RADICALS [J].
ITO, O ;
OMORI, R ;
MATSUDA, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (14) :3934-3937
[8]   TRIS-(TRIMETHYLSILYL)SILANE IN THE DEOXYGENATION OF LONG-CHAIN UNSATURATED ALCOHOLS CONVERTS CIS TO TRANS ISOMERS [J].
JOHNSON, DW ;
POULOS, A .
TETRAHEDRON LETTERS, 1992, 33 (15) :2045-2048
[9]   VINYL RADICALS .4. STEREOCHEMISTRY OF FREE-RADICAL ADDITION OF CHLOROFORM TO ALKYLACETYLENES [J].
KOPCHIK, RM ;
KAMPMEIE.JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (24) :6733-&
[10]   RADICALS FORMED FROM ACETYLENES BY HIGH-ENERGY RADIATION AND HYDROGEN-ATOM BOMBARDMENT - ELECTRON-SPIN RESONANCE STUDY [J].
NEILSON, GW ;
SYMONS, MCR .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1973, (10) :1405-1410