RING EXPANSION OR SPIROCYCLISATION OF (PHENYLTHIOMETHYLENE)CYCLOALKANES WITH ALUMINUM-CHLORIDE VIA BETA-THIO CARBOCATIONS

被引:4
作者
DEROUANE, D [1 ]
HARVEY, JN [1 ]
VIEHE, HG [1 ]
机构
[1] UNIV CATHOLIQUE LOUVAIN,CHIM ORGAN LAB,B-1348 LOUVAIN,BELGIUM
关键词
D O I
10.1039/c39950000993
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The title reactions can be explained by Wagner-Meerwein rearrangement of alpha-thio carbocations (thionium ions) to beta-thio carbocations; this unusual reactivity may be due to superelectrophilic activation by aluminium chloride.
引用
收藏
页码:993 / 994
页数:2
相关论文
共 21 条
[1]  
ABDIN T, 1973, VESTN MOSK U KHIM+, V14, P491
[2]   THE SYNTHESIS OF SPIRO[ADAMANTANE-[1,2]DIOXETANES] [J].
ADAM, W ;
ENCARNACION, LAA .
CHEMISCHE BERICHTE-RECUEIL, 1982, 115 (07) :2592-2605
[3]   THE STABILITIES OF ALPHA-OXY AND ALPHA-THIO CARBENIUM IONS - THE IMPORTANCE OF THE GROUND-STATE ENERGIES OF THE NEUTRAL PRECURSORS [J].
APELOIG, Y ;
KARNI, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1988, (05) :625-636
[4]   STABILITIES OF CARBOCATIONS IN SOLUTION .14. AN EXTENDED THERMOCHEMICAL SCALE OF CARBOCATION STABILITIES IN A COMMON SUPERACID [J].
ARNETT, EM ;
HOFELICH, TC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (09) :2889-2895
[5]  
BOCK H, 1984, Z NATURFORSCH B, V39, P763
[6]   EFFECT OF A BETA-SILYL GROUP ON THE REGIOCHEMISTRY OF ENOLIZATION OF KETONES [J].
ENGEL, W ;
FLEMING, I ;
SMITHERS, RH .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (09) :1637-1641
[7]  
GIESE B, 1981, CHEM BER, V114, P2850
[8]  
GROEN SH, 1968, J ORG CHEM, V33, P780
[9]   ALKYL MIGRATION IN COMPETITION WITH PHENYLTHIO MIGRATION IN THE ACID-CATALYZED REARRANGEMENT OF ALCOHOLS [J].
HANNABY, M ;
WARREN, S .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (22) :3007-3013
[10]   STABILIZATION ENERGY AND ION SIZE IN CARBOCATIONS IN THE GAS-PHASE [J].
LOSSING, FP ;
HOLMES, JL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (23) :6917-6920