Unusual heterocyclisation in the transformation of 6-halomethylsulfonyl-substituted bicyclo[3.1.1]heptane under Ramberg-Backlund reaction conditions

Viktor A. Vasin; Ella V. Romanova; Sergei G. Kostryukov; Vyacheslav V. Razin

doi:10.1070/MC1998v008n03ABEH000913

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DOI: 10.1070/MC1998v008n03ABEH000913 (Paper) Mendeleev Commun., 1998, 8, 122-125

Unusual heterocyclisation in the transformation of 6-halomethylsulfonyl-substituted bicyclo[3.1.1]heptane under Ramberg-Backlund reaction conditions

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Viktor A. Vasin , Ella V. Romanova , Sergei G. Kostryukov and Vyacheslav V. Razin

Abstract

Boiling of exo-6-bromo-syn-7-bromo(chloro)methylsulfonyl-endo-6-phenylbicyclo[3.1.1]heptane in water-dioxane solutions of NaOH results in anti-6-hydroxy-7-methylene-syn-6-phenylbicyclo[3.1.1]heptane according to the Ramberg-Backlund reaction; in addition, a product of unusual heterocyclisation is formed, namely, 3-oxa-2-phenyl-5-thiatricyclo[4.4.0.0^2,7]decane S,S-dioxide.

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