Title: Ortho photocycloaddition of substituted 4-phenoxybut-1-enes. Identification of rearranged photocycloadducts by NMR
Authors: Busson, Roger ×
Schraml, J
Saeyens, W
Van der Eycken, Erik
Herdewijn, Piet
De Keukeleire, D #
Issue Date: Jan-1997
Series Title: Bulletin des Sociétés Chimiques Belges vol:106 issue:11 pages:671-676
Abstract: The ortho photocycloadducts, formed on irradiation of 3-tert-butyl-4-phenoxybut-1-ene (1a) and 3-acetoxy-4-(4-methoxyphenoxy)but-1-ene (1b) at 254 nm, underwent in situ rearrangement to tricyclic structures 4a, 5a, and 5b, 5b', respectively. Hydration of the vinyl ether function in 5a led to 6a, while a similar secondary reaction of 5b afforded 8b. A detailed NMR investigation of the rearranged ortho photocycloadducts of both 1a and 1b revealed not only the relevant structures, but also furnished configurational and conformational details.
ISSN: 0037-9646
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Medicinal Chemistry (Rega Institute)
Molecular Design and Synthesis
× corresponding author
# (joint) last author

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