Summary
Irrespective of the presence or absence of benzoyl peroxide, hydrogen bromide adds to allylchlorosilanes Cln(CH3)3-nSiCH2CH=CH2 exclusively in accordance with Markovnikov's rule when n=0 and 1 and only in the opposite direction when n=3. When n=2, hydrogen bromide may add both in accordance with the rule, and also against the rule when benzoyl peroxide is used. For all values ofn, hydrogen iodide adds to allylchlorosilanes exclusively in accordance with Markovnikov's rule.
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Mironov, V.F. Direction of the addition of HBr and HI to allyl- and (2-methylallyl)-chlorosilanes. Russ Chem Bull 8, 1781–1783 (1959). https://doi.org/10.1007/BF00912124
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DOI: https://doi.org/10.1007/BF00912124