The reaction of lithium phenylacetylide and phenyllithium with N-(ω-Bromoalkyl)phthalimides

Lithium phenylacetylide reacted with short-chain N-(ω-bromoalkyl)phthalimides 1b and 1c to give tricyclic products 2b and 2c in moderate yields. Likewise, tricyclic products 3a-c were obtained when short-chain imides 1a-c were treated with phenyllithium. When longer-chain imides 1d-f in this series were treated with lithium phenylacetylide only tertiary alcohols 4d-f could be isolated. Partial hydrogenation of 2b and 2c yielded the corresponding alkenes 5b and 5c , products which corroborated the structural assignment of 2b and 2c .