STUDIES IN THE TRICYCLOOCTANE SERIES .I. DEHYDROHALOGENATION OF SOME BIS-HALOGENOCARBENE ADDUCTS OF CYCLOHEXADIENES

被引:25
作者
BANWELL, MG [1 ]
HALTON, B [1 ]
机构
[1] VICTORIA UNIV WELLINGTON,DEPT CHEM,WELLINGTON,NEW ZEALAND
关键词
D O I
10.1071/CH9790849
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Reaction between 4, 4, 8, 8-tetrachloro-cis-transoid-cis-tricyclo[5, l, 0, 03, 5]octane (1d) and potassium t-butoxide leads to the (E)- and (Z)-β-t-butoxy-4-chlorostyrenes (8a, b). The epimeric 4, 4, 8-trichloro analogues (1e, f) behave similarly to give (E)-β-t-butoxystyrene (8c) as the sole isolable product in low yield. Under the same conditions the corresponding tri- and tetra-chloro-cis-transoid-cis-tricyclo[5, 1, 0, 02, 4]octanes (7d-f) yield complex product mixtures. Evidence is presented which suggests the non-involvement of halogenocyclooctatetraenes in these reactions. © 1979, CSIRO. All rights reserved.
引用
收藏
页码:849 / 858
页数:10
相关论文
共 38 条
[1]   PREPARATION AND RING FISSION OF SOME BENZOCYCLOBUTENE-1(2H)-ONE DERIVATIVES [J].
AMUPITAN, JO ;
STANSFIE.F .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (16) :1949-1951
[2]  
ARBUZOV BA, 1973, NOV KHIM KARBENOV MA, P194
[3]  
ARCT J, 1977, B ACAD POL SCI-CHIM, V25, P697
[4]   STUDIES IN CYCLOPROPA-ARENE SERIES - APPROACHES TO CYCLOPROPA[A]-NAPHTHALENE [J].
BANWELL, MG ;
BLATTNER, R ;
BROWNE, AR ;
CRAIG, JT ;
HALTON, B .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (19) :2165-2168
[5]   EFFECT OF RING SIZE ON THERMAL REARRANGEMENTS OF BICYCLO[N.1.0]ALKA-1,NORMAL-DIENES [J].
BILLUPS, WE ;
BAKER, BA ;
CHOW, WY ;
LEAVELL, KH ;
LEWIS, ES .
JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (12) :1702-1704
[6]   ROTATIONAL-ISOMERISM OF BICYCLOPROPYL .3. NMR SPECTROSCOPIC INVESTIGATIONS OF 2 CONFORMATIONALLY RESTRICTED BICYCLOPROPYL DERIVATIVES [J].
BRAUN, S ;
LUTTKE, W .
CHEMISCHE BERICHTE-RECUEIL, 1976, 109 (01) :320-328
[7]   COMPETITIVE PATHWAYS IN DEHYDROCHLORINATION ROUTE TO CYCLOPROPA-ARENES [J].
BROWNE, AR ;
HALTON, B .
TETRAHEDRON, 1977, 33 (03) :345-348
[8]  
BUDZIKIEWICZ H, 1967, MASS SPECTROMETRY OR, pCH6
[9]   REDUCTIONS OF TETRAHALO-1,3,5,7-TETRAMETHYL-ANTI-TRICYCLO[5.1.0.03,5]OCTANE-2,6-DIONES.1,3,5,7-TETRAMETHYL-ANTI-TRICYCLO[5.1.0.03,5]OCTANE-2,6-DIONE [J].
CHAPLEO, CB ;
DREIDING, AS ;
DYLLICKBRENZINGER, RA ;
OTH, JFM .
HELVETICA CHIMICA ACTA, 1976, 59 (04) :1311-1327
[10]  
CHAPLEO CB, 1977, HELV CHIM ACTA, V60, P1403