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- Title
Novel Intramolecular Cyclization of 2-(Buta-1,3-dienyl)benzyl Anions to 6,7(9)-Dihydro-5 H-benzocycloheptenyl Anions Leading to Successive Formation of 1,2-Dihydrocyclopropa[ a]naphthalenes.
- Authors
Saitoh, Hisashi; Ijuin, Hisako K.; Watanabe, Nobuko; Matsumoto, Masakatsu
- Abstract
When treated with LiNiPr2 (LDA) at −78°, 1-[(methylsulfanyl)methyl]-2-[(1 Z,3 E)-4-phenylbuta-1,3-dien-1-yl]benzene easily cyclized to form benzocycloheptenyl anion, which successively underwent intramolecular nucleophilic substitution to give a cyclopropanaphthalene. Similar LDA-mediated cyclization also occurred for 4-phenyl- or 4-methyl-substituted 1-[2-(methoxymethyl)phenyl]buta-1,3-dienes to furnish the corresponding benzocycloheptenes and cyclopropanaphthalenes. A 4- tert-butyl analog also underwent LDA-mediated cyclization to give a benzocycloheptene, but not a cyclopropanaphthalene.
- Subjects
BENZOCYCLOHEPTENE; INTRAMOLECULAR catalysis; ANIONS; NAPHTHALENE; METHOXYMETHYL compounds; RING formation (Chemistry)
- Publication
Helvetica Chimica Acta, 2013, Vol 96, Issue 9, p1704
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.201200653