Synthesis of four-membered ring acyloins and α-diketones

✍ Scribed by G.E. Gream; Miss S. Worthley

• Book ID: 104222747
• Publisher: Elsevier Science
• Year: 1968
• Tongue: French
• Weight: 156 KB
• Volume: 9
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)89556-8

✦ Synopsis

The very recent report by Bloomfield (1) that four-membered ring acyloins can be conveniently synthesised via intermediate enediolates as their trimethylsilyl ether derivatives prompts us to communicate some of our results in this field. For some time, we have been attempting to synthesise 3,3,4,4_tetramethylcyclobutanedione (I) (2) as part of our studies on the photochemistry of a-diketones (5), and the synthesis of small ring compounds.

2,2,3,3_Tetramethylcyclobutanone (II) ( ) and the acyloin 2-hydroxy-3,3,4,4tetramethylcyclobutanone (III) seemed to be attractive intermediates for the preparation of (I). Not unexpectedly, attempted synthesis of (III) from dimethyl tetramethylsuccinate