1,1-vs. 1,6-Dehalogenation in gem-dibromocyclopropanes. Synthesis of benzo-anti-σ-bishomobenzene
Abstract
The bisdibromocarbene adduct (9a) on treatment with methyl-lithium at temperatures below ca.–50 °C undergoes a ring-closure reaction by 1,6-elimination to give after reduction anti-σ-bishomobenzene (11); above –50 °C products derived from 1,1-eliminations and subsequent cyclopropyliden(oid)–allene rearrangements dominate.