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Competing solvolysis-decomposition of 1-adamantyl chloroformate

✍ Scribed by Dennis N. Kevill; Frederick L. Weitl

Publisher: Elsevier Science
Year: 1971
Tongue: French
Weight: 204 KB
Volume: 12
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)96537-2

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✦ Synopsis

Recently. the preparation of I-pdprantyl chlorofoxmate was reported2 and the decaqosition of compouud to yield I-adamaatyl chl oride has been studied3. The kiuetic procedure was to bydrothe mmmcted chloroformate ester in aqueous acetone aud titrate against rthauolic sodim methoxide. The 1-adamantyl halide, produced in the decomposition, was inert mder these umditious.

We found that the acid present after hydrolysis was only proportional to, and not equivalent to, the concentration of uuxeacted chloroformate ester. It was apparent that, within the aqueoos acetone, decomposition was effectively cwting with solvolysis.

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