Dichlorocyclopropanation, epoxidation, and subsequent reactions of isotetralin derivatives

Reaction of excess CCl 2 with isotetralin ( 1 ) gives a separable mixture of bis‐ and tris‐adducts 3 – 6 , where 6 exhibits syn ‐standing dichlorocyclopropanes at a six‐membered ring. – Epoxidation of 2a and b furnishes the symmetrical diepoxides 7a and b . With BuLi/CO 2 , 7b afforded the α‐bromo lactone 10 . – From 3 the epoxide 8 is formed which is cleaved to give the diol 11 . – The epoxide 9a proves the anti ‐structure of 4 . – LiAlH 4 reduction of 3 leads by exo ‐attack mainly to a separable mixture of 13 and 14 .