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Synthesis 2001(8): 1143-1148
DOI: 10.1055/s-2001-15058
DOI: 10.1055/s-2001-15058
PAPER
© Georg Thieme Verlag Stuttgart · New York
Regioselectivity of the Intramolecular Photocycloaddition of α,β-Butenolides to a Terminal Alkene
Further Information
Received
1 February 2001
Publication Date:
24 September 2004 (online)
Publication History
Publication Date:
24 September 2004 (online)
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Abstract
The intramolecular [2+2] photocycloaddition of α,β-butenolides to a terminal double bond tethered to the lactone through the γ-position and located at a suitable distance has been studied. The regioselectivity of the photoisomerization depends on the substitution pattern of the substrate and can be rationalized by simple theoretical calculations performed on the diradical intermediates.
Key words
intramolecular photochemical cycloaddition - α,β-butenolides - alkenes - regioselectivity - intermediate diradicals
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