72806-74-7Relevant academic research and scientific papers
SYNTHESIS OF LACTONES BY INTRAMOLECULAR ADDITION OF ALKOXYTHIOCARBONYL FREE RADICALS TO ACETYLENES
Nozaki, Kyoko,Oshima, Koichiro,Utimoto, Kiitiro
, p. 6127 - 6128 (1988)
Lactones are obtained by treating dithiocarbonates of homopropargylic or homoallylic alcohols with n-Bu3SnH-Et3B.
Synthesis of γ- and δ-Lactones by Free-Radical Annelation of Se-Phenyl Selenocarbonates
Bachi, Mario D.,Bosch, Eric
, p. 4696 - 4705 (2007/10/02)
A general method for the synthesis of γ- and δ-lactones through the intramolecular addition of alkoxycarbonyl radicals, formed by reaction of Se-phenylselenocarbonates with n-Bu3SnH, onto carbon-carbon multiple bonds is described.This free-radical cyclization is characterized by high regioselectivity favoring exo addition and by a high ratio of cyclization to reduction.Monocyclic, fused bicyclic, and spirocyclic lactones are formed in good to excellent yield.Use of allyltri-n-butyltin as a chain-transfer agent in the place of n-Bu3SnH affords the corresponding 3-butenyl lactones.
Facile Reduction of Dithiocarbonates Derived from Secondary Alcohols with n-Bu3SnH-Et3B and Synthesis of 2-Furanthiones and 2-Furanones by Intramolecular Addition of Alkoxythiocarbonyl Free Radicals to Acetylenic Linkages
Nozaki, Kyoko,Oshima, Koichiro,Utimoto, Kiitiro
, p. 2578 - 2583 (2007/10/02)
The reduction of dithiocarbonates or thiocarbonates by n-Bu3SnH-Et3B easily gives the corresponding hydrocarbons.The intermediate alkoxythiocarbonyl radical equivalents are trapped by properly located carbon-carbon multiple bonds.The dithiocarbonates derived from either homopropargylic or homoallylic alcohols produce tetrahydrofuranones upon treatment with n-Bu3SnH-Et3B.Application of this new method to the conversion of carbonyl compounds into olefins is also described.
SYNTHESIS OF α-ALKYLIDENE-γ-LACTONES BY INTRAMOLECULAR ADDITION OF ALKOXYCARBONYL FREE-RADICALS TO ACETYLENES
Bachi, Mario D.,Bosch, Eric
, p. 641 - 644 (2007/10/02)
α-Alkylidene-γ-lactones are obtained by treatment of chloroformate and selenocarbonate derivatives of homopropargylic alcohols with tri-n-butylstannane.
