Premium
The reaction of lithium phenylacetylide and phenyllithium with N ‐(ω‐Bromoalkyl)phthalimides
Author(s) -
Torian Bruce E.,
Braun Loren L.
Publication year - 1984
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570210204
Subject(s) - phenyllithium , phthalimides , chemistry , lithium (medication) , chain (unit) , tricyclic , organic chemistry , phthalimide , medicine , physics , astronomy , endocrinology
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 .