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

doi:10.1016/S0040-4039(98)02240-0

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

Institute of Chemistry

Research output: Contribution to journal › Article › peer-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 language	English
Pages (from-to)	9815-9818
Number of pages	4
Journal	Tetrahedron Letters
Volume	39
Issue number	52
DOIs	https://doi.org/10.1016/S0040-4039(98)02240-0
State	Published - 24 Dec 1998

Access to Document

10.1016/S0040-4039(98)02240-0

Cite this

@article{cd6fbffeab584683ad74ed4bdbc54e35,

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

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.",

author = "Shlomo Cohen and Ami Zoran and Yoel Sasson",

year = "1998",

month = dec,

day = "24",

doi = "10.1016/S0040-4039(98)02240-0",

language = "אנגלית",

volume = "39",

pages = "9815--9818",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd.",

number = "52",

}

TY - JOUR

T1 - Direct evidence for the hydroxide extraction mechanism in the phase transfer catalyzed cyclopropanation of 4-halobutyronitrile in a solid-liquid system

AU - Cohen, Shlomo

AU - Zoran, Ami

AU - Sasson, Yoel

PY - 1998/12/24

Y1 - 1998/12/24

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/0032564533

U2 - 10.1016/S0040-4039(98)02240-0

DO - 10.1016/S0040-4039(98)02240-0

M3 - ???researchoutput.researchoutputtypes.contributiontojournal.article???

AN - SCOPUS:0032564533

SN - 0040-4039

VL - 39

SP - 9815

EP - 9818

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 52

ER -

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

Abstract

Access to Document

Other files and links

Fingerprint

Cite this