Abstract
Carbonyl ylides 2, generated by thermolysis of alkoxyoxadiazolines 1 in chloroform, react with chloroform to form ketals (3) of 1,1,1-trichloropropanone. The isotope effect at 80 °C, determined by analysis of products from thermolysis of 1 in mixed solvent (CHCl3/CDCl3, both in large excess) was estimated to be kH/kD = 5. A mechanism involving concerted C—Cl and C—H bond formation between the ylide C atoms and the Cl and H atoms of chloroform is proposed. The ketals of 1,1,1-trichloropropanone are the first to be reported. Key words: carbonyl ylide, reaction with chloroform; chloroform, reaction with carbonyl ylides; ketals, of 1,1,1-trichloropropanone; 1,1,1-trichloropropanone, ketals of.
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