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Novel selective synthesis of α-chloromethyl, α,α-dichloromethyl, and α,α,α-trichloromethyl ketones from aldehyde utilizing electroreduction as key reactions

✍ Scribed by Tatsuya Shono; Naoki Kise; Akira Yamazaki; Hiroshi Ohmizu

Publisher
Elsevier Science
Year
1982
Tongue
French
Weight
216 KB
Volume
23
Category
Article
ISSN
0040-4039

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✦ Synopsis

A variety of a-chloromethyl, a,a-dichloromethyl, and a,o,u-trichloromethyl ketones were synthesized from aldehyde utilizing cathodic reduction as key reactions.

Recently we have found a practically useful electroreductive anionic chain reaction in which aldehyde was efficiently converted into trichloromethylcarbinol 1.

2

In our continuing study on the utilization of 1 in organic synthesis, it was found that 1 could selectively be transformed into o-chloromethyl 4, o,o-dichloromethyl 5, and o,a,a-trichloromethyl 6 ketones as the overall process is shown in Scheme I.

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