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Photochemistry of ω-(o-vinylphenyl)-ω′-(phenyl/2-furyl) butadienes: New approach to 4-substituted benzobicyclo[3.2.1]octadienes

Paper ID Volume ID Publish Year Pages File Format Full-Text
28063 44058 2009 7 PDF Available
Title
Photochemistry of ω-(o-vinylphenyl)-ω′-(phenyl/2-furyl) butadienes: New approach to 4-substituted benzobicyclo[3.2.1]octadienes
Abstract

Novel 1-(o-vinylphenyl)-4-(phenyl/2-furyl) butadienes (4a,b), synthesized in one step, undergo intramolecular photocycloaddition reaction to benzobicyclo[3.2.1]octadiene derivatives (6a,b) in very good yield (70–90%). In the case of phenyl derivative (4a) only endo-phenyl-benzobicyclo[3.2.1]octadiene isomer (endo-6a) was isolated whereas the furan (4b) derivative resulted in a mixture of endo- and exo-bicyclic isomer (6b). Phenyl benzobicyclo[3.2.1]octadiene derivative (endo-6a) underwent further di-π-methane rearrangement leading to tricyclic structure (endo-7a). The isolated compound 6a and the product of the rearrangement endo-7a were characterised by X-ray structure analysis.

Keywords
Cycloaddition; Furan; Di-π-methane rearrangement; Photochemistry
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Photochemistry of ω-(o-vinylphenyl)-ω′-(phenyl/2-furyl) butadienes: New approach to 4-substituted benzobicyclo[3.2.1]octadienes
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 207, Issues 2–3, 25 September 2009, Pages 190–196
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
Get Full-Text Now
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Price was $35.95
You save - $31
Price after discount Only $4.95
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