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Formation and Rearrangement of Cyclic Semi-aminals with α-Mercapto Groups
Kucklaender, Uwe,Edoho, Edoho J.,Rinus, Olaf,Massa, Werner
, p. 3405 - 3415 (2007/10/02)
Reaction of thioacetic acid, thiobenzoic acid as well as 2-aminothiophenol with racemic cyclic semi-aminal 3 takes a diastereoselective course to racemic 4a, b, c.The ambident thiazolidine-2-thione reacts analogously, however by attack of nitrogen yielding 4d.The possibilities for rearrangement of adducts 4 are discussed and the structure of the rearranged products is examinated by x-ray analysis of 9c as well as by 13C NMR spectroscopy.The course of the diastereoselective rearrangement to the racemic mixture (α/β) of 2-azaspirononenes 9a-d is discussed by aid of the results.
