INTRAMOLECULAR CYCLIZATIONS OF ALPHA-STANNYL RADICALS TO ACYLSILANES - REGIOSPECIFIC SYNTHESES OF 5-MEMBERED CYCLIC SILYL ENOL ETHERS

被引:25
作者
TSAI, YM
CHANG, SY
机构
关键词
D O I
10.1039/c39950000981
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
alpha-Stannyl radicals generated from acylsilanes 5, 13 and 14 cyclize to give good yields of cyclic silyl enol ethers after sequential cyclizations, radical Brook rearrangements and beta-scissions.
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页码:981 / 982
页数:2
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共 15 条
[1]  
Cirillo P. F., 1992, ORG PREP P INT, V24, P553
[2]   PREPARATION OF 2-(3-BROMO-1-METHYLPROPYL)-1,3-DIOXOLAN AND THE CORRESPONDING CHLORIDE FROM 2-METHYLBUTYROLACTONE [J].
COLLINS, DJ ;
JAMES, AM .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1989, 42 (01) :223-228
[3]   REMOVAL OF THIOACETAL PROTECTING GROUPS BY CERIUM(IV) AMMONIUM-NITRATE - HYDROLYSIS OF 1,3-DITHIANNES [J].
CRISTAU, HJ ;
CHABAUD, B ;
LABAUDINIERE, R ;
CHRISTOL, H .
SYNTHETIC COMMUNICATIONS, 1981, 11 (06) :423-428
[4]  
CURRAN DP, 1993, SYNLETT, P403
[5]   MECHANISTIC PHOTOCHEMISTRY OF ACYLSILANES .2. REACTION WITH ELECTRON-POOR OLEFINS [J].
DALTON, JC ;
BOURQUE, RA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (03) :699-700
[6]   REACTIONS OF DITHIANE DERIVED ALCOHOLS - PROMOTION OF THE THORPE-INGOLD EFFECT BY TRIMETHYLSILYL AND TERT-BUTYL SUBSTITUENTS [J].
DAVEY, AE ;
PARSONS, AF ;
TAYLOR, RJK .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (10) :1853-1858
[7]   1,2-MIGRATION OF THE TRIMETHYLSILYL GROUP IN FREE-RADICALS [J].
HARRIS, JM ;
MACINNES, I ;
WALTON, JC ;
MAILLARD, B .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1991, 403 (03) :C25-C28
[8]  
HO TL, 1972, J CHEM SOC CHEM COMM, P791
[9]   SYNTHESIS AND CHEMISTRY OF ACYL SILANES [J].
PAGE, PCB ;
KLAIR, SS ;
ROSENTHAL, S .
CHEMICAL SOCIETY REVIEWS, 1990, 19 (02) :147-195
[10]  
RICCI A, 1989, SYNTHESIS-STUTTGART, P647