Radical Cyclizations of Alkenyl Acylphosphonate Derivatives under Thermal and Photochemical Conditions

The use of alkenyl acylphosphonate and acylphosphine oxide derivatives as acceptors in radical cyclizations was studied under thermal and photochemical conditions, respectively. The cyclizations of alkenyl acylphosphonates under thermal conditions occurred smoothly in refluxing dioxane using benzoyl...

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Bibliographic Details
Published inBulletin of the Chemical Society of Japan Vol. 78; no. 9; pp. 1665 - 1672
Main Authors Cho, Chang Ho, Kim, Sunggak, Yamane, Motoki, Miyauchi, Hironori, Narasaka, Koichi
Format Journal Article
LanguageEnglish
Published TOKYO The Chemical Society of Japan 01.09.2005
Chemical Soc Japan
Chemical Society of Japan
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
DIALKYL ACYLPHOSPHONATES
CENTERED RADICALS
CARBONYL GROUP
INTRAMOLECULAR HOMOLYTIC SUBSTITUTION
ACYLATION
ACYL RADICALS
RATE CONSTANTS
EFFICIENT SYNTHESIS
GENERATION
SULFUR
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Summary:The use of alkenyl acylphosphonate and acylphosphine oxide derivatives as acceptors in radical cyclizations was studied under thermal and photochemical conditions, respectively. The cyclizations of alkenyl acylphosphonates under thermal conditions occurred smoothly in refluxing dioxane using benzoyl peroxide as an initiator; the addition of diethyl phosphite increased the chemical yield. Photochemically induced cyclizations of alkenyl acyldiphenylphosphine oxides at 300 nm gave similar results, although a notable difference was observed in one case. The intramolecular cyclization of S-but-3-enyl phosphinothiolformates occurred under thermal and photochemical conditions, providing thiolactones, whereas S-pent-4-enyl phosphinothiolformate afforded the tetrahydrothiophene derivative under similar conditions.
ISSN:0009-2673
1348-0634
DOI:10.1246/bcsj.78.1665