Facile procedure for the hydrolysis of vinyl halides to ketones

✍ Scribed by Stephen F. Martin; Ta-shue Chou

• Publisher: Elsevier Science
• Year: 1978
• Tongue: French
• Weight: 187 KB
• Volume: 19
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)94715-x

✦ Synopsis

The difficulty that may be encountered in the hydrolysis of vinyl halides to give carbonyl compounds (l-+2) frequently vitiates the use of the vinyl halide moiety as a _ _ 1 2 latent carbonyl function in organic synthesis. While a number of procedures may be employed to achieve this important transformation, most require strong acid.' Under these drastic conditions a variety of undesired side reactions may ensue, especially in polyfunctional molecules. Consequently, several methods have been developed in which tranSitiOn metals, including CU(I),~ Ti(rV),3 Hg(II)py5 and Pd(II),5 were used in order to allow the hydrolysis of the vinyl halide to proceed under somewhat milder conditions. During the course of a recent synthetic investigation, we required a mild procedure for the conversion of a-chloroallyl-and cr-chlorocrotylaldehydes and ketones into 1,4-and 1,LGdicarbonyl compounds which were to be used in subsequent annelation operations. Unfortunately, most of the above procedures proved unsatisfactory.6 Considering the ready availability of the starting vinylhalo carbonyl compounds, this limitation in methodology for the hydrolysis of the vinyl halides was particularly frustrating.

We now wish to report that vinyl chlorides may be readily converted into ketones at room temperature using mercuric acetate in either glacial acetic acid containing boron 1943