601491-05-8Relevant academic research and scientific papers
Synthesis and thermal stability of secondary sugar allyltin derivatives
Jarosz, Slawomir,Szewczyk, Katarzyna,Zawisza, Anna
, p. 1715 - 1723 (2007/10/03)
Reaction of sugar allylic mesylates with tri-n-butyltin cuprate affords the primary and secondary allyltin derivatives: Sug-CH=CH-CH2SnBu3 and Sug-CH(SnBu3)-CH=CH2 with the latter predominating. The SN2′ addition led almost exclusively to one isomer with the S configuration at the newly created stereogenic center. Only traces of the opposite R isomer were formed. Both stereoisomers of secondary allyltins decompose at high temperature (140°C) with elimination of the tin moiety and opening of the sugar ring. The main S isomer gives the dienoaldehyde CH2=CH-CH=CH-[(CHOR)3]-CHO with the cis geometry across the internal double bond. The minor R isomer provides the trans dienoaldehyde under the same conditions. These results strongly suggest the concerted (E2) mechanism of thermal decomposition of secondary sugar allyltin derivatives.
