An unexpected involvement of ethyl-2-cyano-2-(hydroxyimino) acetate cleaved product in the promotion of the synthesis of nitriles from aldoximes: A mechanistic perception

Dharm Dev; Nani Babu Palakurthy; Nitesh Kumar; Bhubaneswar Mandal

doi:10.1016/j.tetlet.2013.05.149

An unexpected involvement of ethyl-2-cyano-2-(hydroxyimino) acetate cleaved product in the promotion of the synthesis of nitriles from aldoximes: A mechanistic perception

Dharm Dev, Nani Babu Palakurthy, Nitesh Kumar, Bhubaneswar Mandal

Research output: Contribution to journal › Article › peer-review

18 Scopus citations

Abstract

While attempting to synthesize nitriles from aldoximes using O-sulfonate esters of oxyma [ethyl 2-cyano-2-(hydroxyimino)acetate], an unexpected involvement of oxyma cleaved product in promoting the synthesis of nitriles was observed. Such involvement of the oxyma cleaved product in the reaction mechanism, together with the usual anticipated pathway improved drastically the applicability of the method by reducing the time needed for the reaction to be completed over that of the sulfonyl chlorides. Other advantages of the present protocol are excellent yields in ambient and milder conditions.

Original language	English
Pages (from-to)	4397-4400
Number of pages	4
Journal	Tetrahedron Letters
Volume	54
Issue number	33
DOIs	https://doi.org/10.1016/j.tetlet.2013.05.149
State	Published - 14 Aug 2013
Externally published	Yes

Keywords

Aldoxime
Dehydration
Nitrile
Oxyma
Sulfonate esters

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2013.05.149

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title = "An unexpected involvement of ethyl-2-cyano-2-(hydroxyimino) acetate cleaved product in the promotion of the synthesis of nitriles from aldoximes: A mechanistic perception",

abstract = "While attempting to synthesize nitriles from aldoximes using O-sulfonate esters of oxyma [ethyl 2-cyano-2-(hydroxyimino)acetate], an unexpected involvement of oxyma cleaved product in promoting the synthesis of nitriles was observed. Such involvement of the oxyma cleaved product in the reaction mechanism, together with the usual anticipated pathway improved drastically the applicability of the method by reducing the time needed for the reaction to be completed over that of the sulfonyl chlorides. Other advantages of the present protocol are excellent yields in ambient and milder conditions.",

keywords = "Aldoxime, Dehydration, Nitrile, Oxyma, Sulfonate esters",

author = "Dharm Dev and Palakurthy, {Nani Babu} and Nitesh Kumar and Bhubaneswar Mandal",

note = "Funding Information: We thank the CIF-IITG for NMR, LC–MS; DST (FIST) for single crystal XRD facility and the Department of Science & Technology, India (FAST TRACK scheme, sanction no. SR/FT/CS-011/2008) for financial support. D.D. and N.B.P. thank IIT-Guwahati for fellowship. We also thank Mr. Harikrishna Sahu and Dr. Aditya Narayan Panda for computational calculations. We also thank the reviewers for their constructive suggestions. ",

year = "2013",

month = aug,

day = "14",

doi = "10.1016/j.tetlet.2013.05.149",

language = "English",

volume = "54",

pages = "4397--4400",

journal = "Tetrahedron Letters",

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number = "33",

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TY - JOUR

T1 - An unexpected involvement of ethyl-2-cyano-2-(hydroxyimino) acetate cleaved product in the promotion of the synthesis of nitriles from aldoximes

T2 - A mechanistic perception

AU - Dev, Dharm

AU - Palakurthy, Nani Babu

AU - Kumar, Nitesh

AU - Mandal, Bhubaneswar

N1 - Funding Information: We thank the CIF-IITG for NMR, LC–MS; DST (FIST) for single crystal XRD facility and the Department of Science & Technology, India (FAST TRACK scheme, sanction no. SR/FT/CS-011/2008) for financial support. D.D. and N.B.P. thank IIT-Guwahati for fellowship. We also thank Mr. Harikrishna Sahu and Dr. Aditya Narayan Panda for computational calculations. We also thank the reviewers for their constructive suggestions.

PY - 2013/8/14

Y1 - 2013/8/14

N2 - While attempting to synthesize nitriles from aldoximes using O-sulfonate esters of oxyma [ethyl 2-cyano-2-(hydroxyimino)acetate], an unexpected involvement of oxyma cleaved product in promoting the synthesis of nitriles was observed. Such involvement of the oxyma cleaved product in the reaction mechanism, together with the usual anticipated pathway improved drastically the applicability of the method by reducing the time needed for the reaction to be completed over that of the sulfonyl chlorides. Other advantages of the present protocol are excellent yields in ambient and milder conditions.

AB - While attempting to synthesize nitriles from aldoximes using O-sulfonate esters of oxyma [ethyl 2-cyano-2-(hydroxyimino)acetate], an unexpected involvement of oxyma cleaved product in promoting the synthesis of nitriles was observed. Such involvement of the oxyma cleaved product in the reaction mechanism, together with the usual anticipated pathway improved drastically the applicability of the method by reducing the time needed for the reaction to be completed over that of the sulfonyl chlorides. Other advantages of the present protocol are excellent yields in ambient and milder conditions.

KW - Aldoxime

KW - Dehydration

KW - Nitrile

KW - Oxyma

KW - Sulfonate esters

UR - http://www.scopus.com/inward/record.url?scp=84880042584&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2013.05.149

DO - 10.1016/j.tetlet.2013.05.149

M3 - Article

AN - SCOPUS:84880042584

SN - 0040-4039

VL - 54

SP - 4397

EP - 4400

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 33

ER -

An unexpected involvement of ethyl-2-cyano-2-(hydroxyimino) acetate cleaved product in the promotion of the synthesis of nitriles from aldoximes: A mechanistic perception

Abstract

Keywords

ASJC Scopus subject areas

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