Bulletin of the Chemical Society of Japan p. 4347 - 4352 (1988)
Update date:2022-08-03
Topics:
Yoshida, Hiroshi
Ohtsuka, Hideki
Yoshida, Keisuke
Totani, Yoshiyuki
Ogata, Tsuyoshi
Matsumoto, Kiyoshi
2,3-Diphenyl-, 2-methyl-3-phenyl-, and 2-methyl-3-(4-methylphenyl)cyclopropenone oxime hydrochlorides (3) were prepared in good yields from the corresponding cyclopropenones and hydroxylamine hydrochloride in methanol.The salts 3 reacted with alkyl and aryl isocyanates in the presence of triethylamine to afford 1 : 2 addition products 4,6-diazaspiro<2,3>hexenones in moderate yields.In contrast, acetone, acetophenone, and cyclohexanone oximes reacted with twice excess of methyl isocyanates to give linear 1 : 1 addition products and benzophenone oxime yielded only 1 : 1 addition product.
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