601491-06-9Relevant articles and documents
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.
Synthesis and reactivity of sugar allyltin derivatives
Jarosz,Szewczyk,Zawisza
, p. 985 - 994 (2007/10/03)
Thermal stability of primary sugar allyltin derivatives: Sug-CH=CH-CH 2SnBu3 was studied. These organometallics with a pyranose ring are stable up to at least 214°C (boiling trichlorobenzene), while those with a furanose ring undergo already at 180°C a controlled decomposition with elimination of the tributylstannyl moiety and opening of the five-membered ring. The mechanism of this process is discussed.