38270-70-1Relevant academic research and scientific papers
THE USE OF L-TARTARIC ACID IN THE SYNTHESIS OF ENANTIOMERICALLY PURE COMPOUNDS: SYNTHESIS OF 4-O-BENZYL-2,3-DIDEOXI-L-THREO-HEX-2-ENONO-1,5-LACTONE
Valverde, Serafin,Herradon, Bernardo,Martin-Lomas, M.
, p. 3731 - 3734 (2007/10/02)
The title compound was obtained through a seven steps sequence and using -dimethyl L-tartrate as the starting material (30percent overall yield).The system 2,3-dideoxy-L-threo-hex-2-enono-1,5-lactone is present in several natural compounds.
Reaction of 1,3-dioxolans with Iodine Monochloride: the Scope and Mechanism of Formation of 1,3-dioxolan-2-ylium Dichloroiodates(I)
Goosen, Andre,McCleland, Cedric W.
, p. 977 - 983 (2007/10/02)
Treatment of a series of 2-substituted-4,4,5,5-tetramethyl-1,3-dioxolanes with iodine monochloride afforded the appropriate 2-substituted-4,4,5,5-tetramethyl-1,3-dioxolan-2-ylium dichloroiodate(I) salts in excellent yields.In contrast to the stable 2-aryl-substituted salts, the 2-alkyl and unsubstituted derivatives were relatively labile.While 2-phenyl-1,3-dioxolan and 2-phenyl-1,3-dioxan afforded low yields of unstable salts,crystalline products could not be isolated from 4,5-disubstituted dioxolans.The reaction was inhibited by electron-withdrawing 4- and 5-substituents.From a study of the effects of photolysis and added iodine, the mechanism is proposed to involve a hydride ion transfer.Possible reasons for the formation of dichloroiodate(I) rather then monohalide salts, are outlined.The stability of the 2-aryl-substituted salts is dicussed in terms of charge distribution in the cation and possible aryl-anion interactions.
