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Title: Stereochemical features of meta photocycloadducts derived from 3-alkyl-4-phenoxybut-1-enes
Authors: Van der Eycken, Erik ×
DeKeukeleire, D
DeBruyn, A
VanderEycken, J
Gilbert, A #
Issue Date: Jan-1995
Publisher: Elsevier science bv
Series Title: Recueil des travaux chimiques des pays-bas-journal of the royal netherlands chemical society vol:114 issue:11-12 pages:480-&
Abstract: 3-Alkyl-4-phencxybut-1-enes (alkyl: methyl, isopropyl, tert-butyl) On excitation at 254 nm in cyclohexane give rise to 4-alkyl-2-oxatetracyclo[5.4.0.0(1.8).0(5,11)]undec-9-enes via intramolecular meta photocycloaddition. Prevailing stereochemical features are the configuration of the alkyl group at C-4 and the conformation of the tetrahydropyran ring contained in the tetracyclic system. These are revealed by detailed H-1-NMR analysis and interpretation of the coupling constants. Whereas the alkyl group at C-4 invariably occurs in the exo configuration, the conformation of the tetrahydropyran ring depends on the bulkiness of the alkyl substituent. Thus, the C-l methyl group occupies an equatorial position in a chair conformation, while a flattened chair conformation accomodates appropriately the C-4 isopropyl group in the pertaining structure. The required equatorial position of the tert-butyl group at C-4. on the other hand, forces the tetrahydropyran ring into a boat conformation, thereby alleviating steric constraints.
ISSN: 0165-0513
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Molecular Design and Synthesis
× corresponding author
# (joint) last author

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