Grignard Reaction and Products. II. A Novel Intramolecular Cyclization in the Grignard Reaction of Alicyclic Ketoxime containing an Aromatic Nucleus

Abstract

A novel intramolecular cyclization reaction was found in the reaction of 2 (1'-phenyl)-cyclohexylcyclohexanone oxime (I-oxime) with aromatic Grignard reagent, either phenyl- or p-tolylmagnesium bromide, which worked as a catalyst. The reaction required at least 3 equivalent moles of Grignard reagent. The structure of the cyclization product (II) was established as spiro [bicyclo [3.3.1]-3, 4-benzononan-9-one-2, 1'-cyclohexane]. The structural feature of oximes which suffer the cyclization reaction was preliminary discussed.