Synthesis of a stable cyclopropene fused by a six-membered ring. A novel approach from fused thiirene sulfoxide
Synthesis of a stable cyclopropene fused by a six-membered ring. A novel approach from fused thiirene sulfoxide
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六元环稠合的稳定环丙烯的合成。
DOI：
10.1021/ja00319a055
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发表时间：
1984
影响因子：
15
通讯作者：
K. Ueno
中科院分区：
文献类型：
--
作者：
W. Andō;Y. Hanyu;T. Takata;K. Ueno
图1.双环[4.1]的分子结构的分步图。8.键长（C1-C2 1.521，C1-C3 1.526，C2-C3 1.286，C2-C4 1.491，C3-C5 1.478）。键角（）：C2-CrC 3 49.92，C1-C2-C3 64.82，C1-C3-C2 65.26，C2-C3-C5 130.23，C3-C2-C4 129.16。所有的双环烯烃1应该具有非平面结构。已经针对双环烯烃的制备进行了相当大的努力。1· 4双环-[4.1. 0]Gassman 6和Wiberg提出了由相应的卤化物脱卤化氢和脱卤化产生的烯烃5Id 6· 7以及la，8lb，9和lc，7作为捕获的Diels-Alder加合物。[7] Closs和Boll在-35 ℃以下对二甲基衍生物2进行了光谱鉴定。10然而，由于其不稳定性，从未报道过1的实验结构研究。
Figure 1. ortep drawing of the molecular structure of bicyclo [4.1. 0]-hex-l (6)-ene 8. Bond lengths (Á): C,-C2 1.521, C,-C3 1.526, C2-C3 1.286, C2-C4 1.491, C3-C5 1.478. Bond angles (): C2-CrC3 49.92, C,-C2-C3 64.82, C,-C3-C2 65.26, C2-C3-C5 130.23, C3-C2-C4 129.16. all bicyclic alkenes 1 should have nonplanar structures. Considerably efforts have been directed toward the preparation of bicyclic alkenes. 1· 4 Evidence for intermediacy of bicyclo-[4.1. 0] alkene5 Id6· 7 as well as la, 8 lb, 9 and lc, 7 produced by dehydrohalogenation and dehalogenation of the corresponding halides, was presented as trapped Diels-Alder adducts by Gassman6 and Wiberg. 7 The dimethyl derivative 2 was spectroscop-ically identified below-35 C by Closs andBoll. 10 However, experimental structural studieshave never been reported for 1 owing to their instability.