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Conversion of 7-substituted norbornadienes to tropyl derivatives: a novel anion-induced rearrangement.

✍ Scribed by Boris Franzus; W.C. Baird Jr.; Robin E. Felty; John C. Smith; Monte L. Scheinbaum

Publisher: Elsevier Science
Year: 1971
Tongue: French
Weight: 200 KB
Volume: 12
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)96423-8

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✦ Synopsis

The isomerization of norbornadiene to cycloheptatriene takes place under relatively severe thermal conditions (425");3 however 7-alkoxy or 7-phenyl substituted norbornadienes undergo a more facile (170") thermal rearrangement to the corresponding tropyl derivative. 4 A similar reaction involving conversion of a norbornadiene system into a cycloheptatriene, occurring under milder ccnditions, was observed in the reduction of 7-acetoxynorbornadiene (I) with lithium aluminum hydride in tetrahydrofuran. 5 The product obtained in this reaction to other ment with leaving 1. Esso Research 2. Taken in part J. C. S. No.4 nucleophiles and to examine the potentiality for rearrangegroups other than hydroxyl or acetyl.

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