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3′‐Keto‐1‐nitro‐2‐phenylspiro[cyclopropane‐3,2′‐quinuclidine]: Synthesis and reactions with nucleophiles
Author(s) -
Besidsky Yevgeny,
Luthman Kristina,
Hacksell Uli
Publication year - 1994
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570310604
Subject(s) - cyclopropane , chemistry , quinuclidine , nucleophile , nitro , ring (chemistry) , medicinal chemistry , trimethylsilyl cyanide , methoxide , lithium (medication) , stereochemistry , organic chemistry , methanol , catalysis , alkyl , medicine , endocrinology
3′‐Keto‐1‐nitro‐2‐phenylspiro[cyclopropane‐3,2′‐quinuclidine] was synthesized by a two‐step procedure from 2‐benzylidenequinuclidin‐3‐one. Ring‐opening reactions of the cyclopropane ring using a variety of N ‐, O ‐, and C ‐nucleophiles (amines, methoxide, nitromethanate, cyanide anions, and lithium diphenylcopper) were studied, and a general mechanism for the transformations is proposed.