Synthesis and hydrolysis of hindered 2, 2-disubstituted 5-cyanocyclopentanonimines

SS Kulp, J Molnar, PJ Miller…

Index: Kulp,S.S. et al. Journal of Organic Chemistry, 1971 , vol. 36, # 15 p. 2203 - 2204

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Citation Number: 3

Abstract

Previous attempts to hydrolyze 2, 2-diphenyl-5-cyanocyclopentanoneimine (Ia, 2-amino-1- cyano-3, 3-diphenylcyclopentene) to 2, 2-dipheny1-5-cyanocyclo-pentanone (Ib) were unsuc~ essful.~~~ The products isolated were the corresponding iminoamide, ketoamide, or decarboxylated ketone. Thus, the normally observed preferential hydrolysis of ketimine before nitrile was reversed in this case. The steric hindrance of the gem phenyl groups ...