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

Abstract

Previous attempts to hydrolyze 2,2-diphenyl-5cyanocyclopentanoneimine (la, 2-amino-l-cyano-3,3diphenylcyclopentene) to 2,2-dipheny 1-5-cyanocyclopentanone (lb) were unsuccessful.2,3 The products

Cyclic Oxonitriles: Synergistic Juxtaposition of Ketone and Nitrile Functionalities

“…Sterically hindered enaminonitriles are sometimes reluctant to hydrolyze, in which case the hydrolysis is best performed with HCl in dioxane to minimize deleterious nitrile hydrolysis. 19 Although illustrated for five-membered oxonitriles, the base-induced cyclization of dinitriles, the Thorpe-Ziegler reaction, provides a powerful method of assembling diverse oxonitriles with 5-to 33-membered rings. I n c r e a s i n g p r o p e n s i t y t o w a r d m e n o l i z a t i o…”

Synthesis and enol determinations of 2,2-disubstituted 6-cyanocyclohexanones

“…Synthesis and Enol Determinations of 2,2-Disubstituted 6-Cyanocyclohexanones (Me, Ph), 13 (CH2CH2Ph, Ph), 10 (Et, Ph), 10 (Pr, Ph), 10 (Am, Ph), 6 (¿-Bu, Ph), 6 (c-Hex, Ph), 5 (¿-Pr, Ph), 4 (CH2Ph, Ph), and 5 (rc-Bu, Ph). The series can be classified in four categories by percentage: A, only parent compound, ~37; B, four compounds, ~20; C, four compounds, ~10; and D, five compounds, ~5.…”