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Reaction of dibenzalcyclohexanone with hydroxylamine hydrochloride. 2D NMR elucidation of the structure of the products

✍ Scribed by Eduardo Dlaz; Héctor Barrios; Benjamin Ortiz; Rubén Sánchez-Obregón; Francisco Yuste; W. F. Reynolds; Jose Luis Aguilera; Efrén Caballero

Publisher
John Wiley and Sons
Year
1989
Tongue
English
Weight
370 KB
Volume
27
Category
Article
ISSN
0749-1581

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✦ Synopsis

The reaction of dibenzalcyclohexanone with hydroxylamine hydrochloride affords three compounds: the oxime of 2-benzylidenecyclohexanone (Z), 3-phenyl-7-benzylidene-3,3a,4,5,6,7-hexahydr~2,l-ben~soxazole (3) and 3-phenyl-3,3a,4,5,6,7-hexahydro-2,l-ben~soxazol~7~pir~~~~-phenylaziridine) (4). Their structures were deduced by 2D NMR analysis. Single-crystal x-ray diffraction was used to confirm the structure and stereochemistry of 4. A possible mechanism for this reaction is proposed.

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