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Cyclopropylmethyl halides, reaction with

Scheme 6. Reactions of the enantiomerically enriched silyllithiiun compound 4 with cyclopropylmethyl halides. Scheme 6. Reactions of the enantiomerically enriched silyllithiiun compound 4 with cyclopropylmethyl halides.
Table 2. Yields and enantiomeric ratios of 14 and 15 from the trapping reactions of 4 with cyclopropylmethyl halides. Table 2. Yields and enantiomeric ratios of 14 and 15 from the trapping reactions of 4 with cyclopropylmethyl halides.
A new decarboxylative route to free radicals, which has proved particularly successful in preparative work, embodies the thermal (or photochemical) decomposition reaction of 1-hy-droxypyridine-2(l/f)-thione esters 23 with tributyltin hydride, /er/-butanethiol, or a similar hydrogen donor.These esters can be easily prepared from acyl halides and the sodium salt of l-hydroxypyridine-2(l//)-thione, or from the carboxylic acid, dicyclohexylcarbodiimide and l-hydroxypyridine-2(l/f)-thione. The intermediate radicals were readily reduced to the corresponding hydrocarbons 24 in efficient chain reactions with organotin hydrides or thiols as reaction partners, and the proportion of rearranged to unrearranged products could be controlled by the choice of hydrogen donor, its concentration and the temperature. This system was sufficiently quantitative and well behaved for use in kinetic studies, and the rate constants of the (S-scission reactions of the listed cyclopropylmethyl species were determined. [Pg.2501]


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Cyclopropylmethyl

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