Regioselectivity of the intramolecular photocycloaddition of α,β-butenolides to a terminal alkene

F. Busquéa; P. De March; M. Figueredo; J. Font; P. Margaretha; J. Raya

Regioselectivity of the intramolecular photocycloaddition of α,β-butenolides to a terminal alkene

F. Busquéa, P. De March, M. Figueredo, J. Font, P. Margaretha, J. Raya

Department of Chemistry

Research output: Contribution to journal › Article › Research › peer-review

14 Citations (Scopus)

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.

Original language	English
Pages (from-to)	1143-1148
Journal	Synthesis
Issue number	8
Publication status	Published - 10 Jul 2001

Keywords

α,β-Butenolides
Alkenes
Intermediate diradicals
Intramolecular photochemical cycloaddition
Regioselectivity

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title = "Regioselectivity of the intramolecular photocycloaddition of α,β-butenolides to a terminal alkene",

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.",

keywords = "α,β-Butenolides, Alkenes, Intermediate diradicals, Intramolecular photochemical cycloaddition, Regioselectivity",

author = "F. Busqu{\'e}a and {De March}, P. and M. Figueredo and J. Font and P. Margaretha and J. Raya",

year = "2001",

month = jul,

day = "10",

language = "English",

pages = "1143--1148",

journal = "Synthesis",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

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TY - JOUR

T1 - Regioselectivity of the intramolecular photocycloaddition of α,β-butenolides to a terminal alkene

AU - Busquéa, F.

AU - De March, P.

AU - Figueredo, M.

AU - Font, J.

AU - Margaretha, P.

AU - Raya, J.

PY - 2001/7/10

Y1 - 2001/7/10

N2 - 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.

AB - 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.

KW - α,β-Butenolides

KW - Alkenes

KW - Intermediate diradicals

KW - Intramolecular photochemical cycloaddition

KW - Regioselectivity

M3 - Article

SP - 1143

EP - 1148

JO - Synthesis

JF - Synthesis

SN - 0039-7881

IS - 8

ER -