Peroxides reaction with Grignard reagents

In the initial discovery of the asymmetric synthesis of a-chloro boronic esters 3, the diastereomeric ratios of 3 were estimated by reaction with Grignard reagents to form secondary alkyl boronic esters 5 and deboronation with hydrogen peroxide to secondary alcohols of known absolute configuration and rotation40. 

Electrophilic hydroxylationReaction of this peroxide (1) with Grignard reagents affords the corresponding silyloxy derivatives in 70-90% yield. The reaction with vinyl Grignard reagents results in silyl enol ethers or a-silyloxy ketones. 

ACGIH TLV 0.1 ppm DOT CLASSIFICATION 2.2 Label Nonflammable Gas SAFETY PROFILE Mildly toxic by inhalation. Explosive reaction with Grignard reagents (e.g., phenylmagnesium bromide). Reacts with tetrafluorethylene + air to form explosive peroxides. When heated to decomposition it emits toxic fumes of F". 

Decomposition of azo compounds and peroxides provides the alkoxyamine by the nitroxide-trapping of the primary radicals [29]. The radicals produced by hydrogen abstraction with oxy radicals are also trapped by the nitroxide [242, 243]. In the photoreaction, alkoxyamines were isolated with high yields [244]. The reactions of Grignard reagents with nitroxides [215] and the coupling reaction of sodium nitroxides with bromo compounds [234,235] are also used. The hydrolysis of 56 followed by the reaction with acyl or alkyl halides afforded alkoxyamines with various functional groups,63 (Eq. 68) [245-251] ... 

Mild oxidation of 3-substituted quinoxalin-2-ones, formed by reaction of quinoxalin-2(l//)-ones and Grignard reagents, with potassium hexacyanoferrate(III) or hydrogen peroxide gives aromatic systems. ... 

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