88986-45-2Relevant articles and documents
Radical cyclizations of alkenyl acylphosphonate derivatives under thermal and photochemical conditions
Cho, Chang Ho,Kim, Sunggak,Yamane, Motoki,Miyauchi, Hironori,Narasaka, Koichi
, p. 1665 - 1672 (2007/10/03)
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 occurre
New radical reactions of S-alkoxycarbonyl xanthates. Total synthesis of (±)-cinnamolide and (±)-methylenolactocin
Forbes, Judith E.,Saicic, Radomir N.,Zard, Samir Z.
, p. 3791 - 3802 (2007/10/03)
Irradiation with visible light of S-alkoxycarbonyl xanthates derived from various alcohols gives rise to alkoxycarbonyl radicals with bifurcate reactivity: loss of carbon dioxide leads to deoxygenated derivatives (i.e. alkyl xanthates) whereas intramolecular addition to a suitably located double bond produces lactones; these new reactions were applied to the total synthesis of (±)-cinnamolide and (±)-methylenolactocin.
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.