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 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.
Publisher
Chemical Soc Japan
Issue Date
2005-09
Language
ENG
Keywords

INTRAMOLECULAR HOMOLYTIC SUBSTITUTION; ACYL RADICALS; EFFICIENT SYNTHESIS; CENTERED RADICALS; DIALKYL ACYLPHOSPHONATES; ACYLATION APPROACH; THIOESTER GROUP; RATE CONSTANTS; CARBONYL GROUP; SULFUR

Citation

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, v.78, no.9, pp.1665 - 1672

ISSN
0009-2673
DOI
10.1246/bcsj.78.1665
URI
http://hdl.handle.net/10203/87468
Appears in Collection
NE-Journal Papers(저널논문)
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