Abstract

Phenylethynyl sulfones of the general formula RSO₂C≡CPh (R = p-Tol, Ph, CH₃) undergo a photochemically induced anti-stereoselective addition to the central C¹–C⁷ bond of 1-bromotricyclo[4.1.0.0^2,7]heptane to form monoadducts of the bicyclo[3.1.1]heptane (norpinic) series containing a syn-sulfonyl group in position 7 and a phenylethynyl moiety on C⁶. Treatment of the synthesized adducts with potassium tert-butylate in THF leads to 1,3-dehydrobromination to give sulfonyl-substituted 1-(phenylethynyl)tricyclo[4.1.0.0^2,7]heptanes.

中文翻译：

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1-溴三环[4.1.0.0 2,7]庚烷与苯乙炔基砜的自由基反应

摘要

通式苯基乙炔基砜RSO ₂ C≡CPh（R = p -Tol中，Ph，CH ₃）经历光化学诱导抗-stereoselective除了中央Ç ¹ -C ⁷键1- bromotricyclo [4.1.0.0的^{2， 7}庚烷形成双环[3.1.1]庚烷（降冰片烯）系列的单加合物，在7位含有一个顺磺酰基和一个在C ⁶上的苯基乙炔基部分。用叔丁醇钾在THF中处理合成的加合物导致1，3-脱氢溴化，得到磺酰基取代的1-（苯基乙炔基）三环[4.1.0.0 ^2,7 ]庚烷。