Novel Intramolecular Cyclization of 2-(Buta-1,3-dienyl)benzyl Anions to 6,7(9)-Dihydro-5H-benzocycloheptenyl Anions Leading to Successive Formation of 1,2-Dihydrocyclopropa[a]naphthalenes

Novel Intramolecular Cyclization of 2-(Buta-1,3-dienyl)benzyl Anions to 6,7(9)-Dihydro-5H-benzocycloheptenyl Anions Leading to Successive Formation of 1,2-Dihydrocyclopropa[a]naphthalenes

When treated with LiNiPr2 (LDA) at −78°, 1‐[(methylsulfanyl)methyl]‐2‐[(1Z,3E)‐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...

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Veröffentlicht in:Helvetica chimica acta 2013-09, Vol.96 (9), p.1704-1713
Hauptverfasser: Saitoh, Hisashi, Ijuin, Hisako K., Watanabe, Nobuko, Matsumoto, Masakatsu
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Benzocycloheptene
Cycloheptatrienyl anion
Cyclopropanaphthalene
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container_issue 9
container_start_page 1704
container_title Helvetica chimica acta
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creator Saitoh, Hisashi
Ijuin, Hisako K.
Watanabe, Nobuko
Matsumoto, Masakatsu
description When treated with LiNiPr2 (LDA) at −78°, 1‐[(methylsulfanyl)methyl]‐2‐[(1Z,3E)‐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.
doi_str_mv 10.1002/hlca.201200653
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subjects Benzocycloheptene
Cycloheptatrienyl anion
Cyclopropanaphthalene
title Novel Intramolecular Cyclization of 2-(Buta-1,3-dienyl)benzyl Anions to 6,7(9)-Dihydro-5H-benzocycloheptenyl Anions Leading to Successive Formation of 1,2-Dihydrocyclopropa[a]naphthalenes
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