Peroxymercuration alkenes

In a process known as peroxymercuration, hydrogen peroxide and alkyl hydroperoxides can be alkylated by alkenes in the presence of a suitable mercury(II) salt... [Pg.144]

The peroxymercuration-demercuration of alkenes provides a more versatile approach to the corresponding hydroperoxides or dialkyl peroxides than direct acid-catalyzed addition (equation 239).372 374... [Pg.306]

A wide variety of alkenes undergo Maikovnikov peroxymercuration. Even a,(3-unsaturated carbonyl compounds afford peroxymercurials whose regiochemistry is dependent on the substitution pattern about the C—C double bond.37 "381 Selective anti addition to the double bond of simple alkenes is the general rule.373 382... [Pg.306]

Alkyl hydroperoxides. Peroxymercuration of alkenes proceeds cleanly and in good yield. These products previously were reduced to the desired alkyl hydroperoxides with alkaline sodium borohydride. This reduction proceeds in reasonable yield in the case of terminal alkenes, but scission to form epoxides of the original alkene predominates among products from nonterminal alkenes. This difficulty is now overcome by use of tri-n-butyltin hydride for reduction.18... [Pg.617]

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