Butylmagnesium reaction + vinyl chloride

On the other hand, butyllithium-aluminum alkyl-initiated polymerizations of vinyl chloride are unaffected by free-radical inhibitors [313]. Also the molecular weights of the resultant polymers are unaffected by additions of CCI4 that acts as a chain transferring agent in free-radical polymerizations. This suggests an ionic mechanism of chain growth. Furthermore, the reactivity ratios in copolymerization reactions by this catalytic system differ from those in typical free-radical polymerizations [313]. An anionic mechanism was also postulated for polymerization of vinyl chloride with f-butylmagnesium in tetrahydrofuran [314]. 

Polarization also occurs in coupling and disproportionation reactions of Grignard reagents with alkyl halides. The vinyl protons of isobutene produced in the reaction of t-butylmagnesium chloride with t-butyl bromide show A/E polarization as do the methyl protons of isobutane (Ward et al., 1970). Similar results arise in the reaction of diethyl-magnesium with organic halides (Kasukhin et al., 1972). 

The synthesis starts from thebeine, which is subjected to a Diels-Alder reaction with methyl vinyl ketone and then reacted with n-butylmagnesium chloride. Finally, in a nucleophilic substitution, the methoxy-group is replaced by hydroxy. 

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