20237-22-3Relevant academic research and scientific papers
THE STERIC COURSE OF THE REACTIONS OF 2,3-DIHALOTETRAHYDROPYRANS WITH GRIGNARD REAGENTS
Berti, Giancarlo,Catelani, Giorgio,Monti, Luigi,Ventresca, Giovanni
, p. 3973 - 3980 (2007/10/02)
The steric course of some reactions of 2,3-dihalotetrahydropyrans with sodium methoxide and with methyl- and phenyl-magnesium bromides has been reinvestigated.Whereas the methanolysis of the cis- and trans-dichlorides occurs with practically complete inversion, it has been confirmed that their reactions, as well as those of dibromides, with methylmagnesium bromide are non-stereospecific, yielding mixtures of trans- and cis-3-halo-2-methyl-tetrahydropyrans in ratios that are independent of the configurations of the starting dihalides.It has been further established that grignard reagents cause equlibration of cis- and trans-dihalide mixtures in a reaction that is much faster than the Grignard coupling step.
