PREPARATION OF DONOR-ACCEPTOR-SUBSTITUTED VINYLCYCLOBUTANES

被引:9
作者
GRUSECK, U [1 ]
HEUSCHMANN, M [1 ]
机构
[1] UNIV MUNICH,INST ORGAN CHEM,KARLSTR 23,W-8000 MUNICH 2,GERMANY
关键词
Vinylcyclobutanes; conformational analysis of; Wittig reaction; Wittig‐Horner reaction; 2+2] Cycloaddition;
D O I
10.1002/cber.19901230924
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
2‐Methylen‐1,3‐dioxolane (1) and the methyl acrylates or crotonates 2 form [2+2] cycloadducts 3 which are reduced to give alcohols 6. Oxidation of these alcohols at low temperatures leads to unstable aldehydes 7, which either rearrange to dihydropyrans 5 or react with Wittig(‐Horner) reagents to afford donor‐acceptor‐substituted vinylcyclobutanes 8. The cis‐vinylcyclobutane 8g is prepared by [2+2] cycloaddition of dioxolane 1 and methyl (2E,4Z)‐hexadienoate (9). The configurations and preferred conformations of the vinylcyclobutanes 8 have unequivocally been assigned on the basis of 13C‐and 1H‐NMR spectra. Copyright © 1990 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim
引用
收藏
页码:1905 / 1909
页数:5
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