Metalated Nitrogen Derivatives of Carbonic Acid in Organic Synthesis, XVI. - Synthesis of 2-Alkylimino- and 2-Arylimino-1,3-oxathiolanes from Lithiated S,S'-Dialkyl Imidodithiocarbonates and Carbonyl Compounds
S,S'-Dialkyl N-(methyl)-, N-(phenyl)-, or N-(cyclopropyl)imidodithiocarbonates 5 were deprotonated by means of lithium diisopropylamide.The resulting α-thio-substituted lithium alkanides 6, which are stabilized by chelatization, were trapped as trimethylsilanes 7.Reaction of 6 with aldehydes or ketones yields the title compounds 20 via adducts 18 and loss of methanethiolate.
Hoppe, Dieter,Follmann, Rainer,Beckmann, Ludger
p. 1765 - 1778
(2007/10/02)
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