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Structure of the 2:2 condensation product of nitromethane and cyclohexanone

✍ Scribed by Wayland E. Noland; Richard J. Sundberg

Book ID
104212528
Publisher
Elsevier Science
Year
1962
Tongue
French
Weight
277 KB
Volume
3
Category
Article
ISSN
0040-4039

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✦ Synopsis

NITROMETHANE and cyclohexanone condense in refluxing solution in the presence of secondary amines to a colorless 212 product C14H20N203 (I), m.p. 270-271' (sublimes). 2,3' Secondary amines used as catalysts include piperidine4 (8-14,3 24s5 yield), piperazine (47$),5 pyrrolidine (23%),5 morpholine (22$), 5 diethylamine (19$), 2 and di-n-propylamine, 3 but the primary amine, methylamine, gave no I. 4 Compound I has also been obtained from condensation of nitromethane with the other reaction products, ' 1-(nitromethyl) cyclohexanol (4% yield),2 and 1-(nitromethyl)cyclohexene, 3 and with the enamines 1-piperidinocyclohexene (lO$)6 and 1,4-bis(l-cyclohexenyl)piperazine (23$).5* Compounds analogous to I have been obtained from secondary aminecatalyzed condensations of nitromethane with 3methyl (1% yield),' L-methyl

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