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Effect of Base and Acyl Chloride on Regioselectivity of Acylation of 8,8-Pentamethylene-2-methyl-7,9-dioxa-1-azaspiro[4.5]dec-1-ene 1-Oxide

Koszytkowska-Stawińska M., Gębarowski P., Sas W.

Polish Journal of Chemistry

2004

Vol. 78 / nr 2

217-222

Acylation of 2-methyl-7,9-dioxa-1-azaspiro[4.5]dec-1-ene 1-oxide (5) in the presence of pyridine gives 3-acyloxy-2-methyl-1-pyrroline derivatives 6 independently of kind of acid chloride, while treatment of 5 with benzoyl or p-nitrobenzoyl chloride and triethylamine affords mainly 2-benzoyloxymethyl- 8a and 2-p-nitrobenzoyloxymethyl-1-pyrroline 8b, respectively. Acetylation of 5 was base-independent.