Tetrahedron p. 3973 - 3980 (1986)
Update date:2022-07-29
Topics:
Berti, Giancarlo
Catelani, Giorgio
Monti, Luigi
Ventresca, Giovanni
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.
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