Direct evidence for the hydroxide extraction mechanism in the phase transfer catalyzed cyclopropanation of 4-halobutyronitrile in a solid-liquid system

Shlomo Cohen, Ami Zoran, Yoel Sasson*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

14 Scopus citations

Abstract

The Hoffman degradation reaction is proposed as an unequivocal proof for the validity of the extraction mechanism in Phase Transfer Catalysis (PTC) in the presence of solid NaOH. 4-Chlorohutyronitrile is found to yield cyclopropyl cyanide via an extraction route while 4-bromobutyronitrile reacts to form the same product by the prevalent interfacial mechanism.

Original languageEnglish
Pages (from-to)9815-9818
Number of pages4
JournalTetrahedron Letters
Volume39
Issue number52
DOIs
StatePublished - 24 Dec 1998

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