Tert-Butylmercuric chloride

The alkylmercuric halides, on the other hand, reacted slowly enough with ozone to permit kinetic studies. While attempts were made to monitor ozone uptake during the first part of the reactions, it was clear that the primary and secondary alkylmercuric halides formed many ozone-reactive intermediates soon after the introduction of 03/02. Hence, in the case of isopropylmercuric chloride (Reaction 10, Table II), isopropyl alcohol was formed and had begun to react appreciably with ozone well before the mercurial had half reacted. By comparison, the reaction of tert-butylmercuric chloride was considerably faster than the primary and secondary alkylmercuric halides (Table III). In this case an excellent 1 1 correlation with ozone was noted throughout the majority of the reaction. Only at the end of this reaction, when other organic products began to appear (NMR), did the reaction mixture demand more than one equivalent of ozone. 

The tertiary alkylmercuric halide, terf-butylmercuric chloride yielded only tert-butyl alcohol as the primary product. It was not until all the organomercurial had reacted that acetone appeared as a reaction product (see Reaction 17, Table I). Thus it again is suggested that an alcohol is the immediate product of C-Hg cleavage by ozone, at least in the case of alkylmercuric halides. 

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See also in sourсe #XX -- [ ]

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