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

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 .