A brief synthesis of endo-2-bromo-5-thiabicyclo [2.1.1]hexane (9) has been developed involving conversion of 3-cyclopentenol (6) to 3-thioacetoxycyclopentene (7), bromination of this giving trans-1,2-dibromo-4-thioacetoxycyclopentane (8), and treatment of the latter with base. Compound 9 is oxidized to its S-oxide 10 and S, S-dioxide 11. Comparative 13C and 1H NMR data are given for 9–11.

This study presents a brief synthesis of endo-2-bromo-5-thiabicyclo [2.1.1]hexane (9) from 3-cyclopentenol (6), 3-thioacetoxycyclopentene (7), and trans-1,2-dibromo-4-thioace

Paper

Simple synthesis of endo-2-bromo-5-thiabicyclo[2.1.1]hexane†

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