A Synthesis of α,β-Unsaturated Ketones from α,β-Unsaturated Nitriles

Randall R. Wroble; David S. Watt

doi:10.1021/jo00879a037

A Synthesis of α,β-Unsaturated Ketones from α,β-Unsaturated Nitriles

Randall R. Wroble, David S. Watt

Molecular and Cellular Biochemistry

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

21 Scopus citations

Abstract

An effective sequence for the synthesis of α,β-unsaturated ketones involves (1) the Horner-Emmons modification of the Wittig reaction to synthesize α,β-unsaturated nitriles, R₂CH₂(R₁)C=C(R₃)CN, from carbonyl compounds, R₂CH₂COR₁, and (2) the oxidative decyanation of the α,β-unsaturated nitriles to afford.ß-unsaturated ketones, R₂CH=C(R₁)COR₃, by sequential treatment with lithium diisopropylamide, oxygen gas, sodium sulfite, and sodium hydroxide.

Original language	English
Pages (from-to)	2939-2940
Number of pages	2
Journal	Journal of Organic Chemistry
Volume	41
Issue number	17
DOIs	https://doi.org/10.1021/jo00879a037
State	Published - Aug 1 1976

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1021/jo00879a037

Cite this

@article{6f51d538fa2340d7a69288c5a0826b23,

title = "A Synthesis of α,β-Unsaturated Ketones from α,β-Unsaturated Nitriles",

abstract = "An effective sequence for the synthesis of α,β-unsaturated ketones involves (1) the Horner-Emmons modification of the Wittig reaction to synthesize α,β-unsaturated nitriles, R2CH2(R1)C=C(R3)CN, from carbonyl compounds, R2CH2COR1, and (2) the oxidative decyanation of the α,β-unsaturated nitriles to afford.{\ss}-unsaturated ketones, R2CH=C(R1)COR3, by sequential treatment with lithium diisopropylamide, oxygen gas, sodium sulfite, and sodium hydroxide.",

author = "Wroble, {Randall R.} and Watt, {David S.}",

year = "1976",

month = aug,

day = "1",

doi = "10.1021/jo00879a037",

language = "English",

volume = "41",

pages = "2939--2940",

number = "17",

}

TY - JOUR

T1 - A Synthesis of α,β-Unsaturated Ketones from α,β-Unsaturated Nitriles

AU - Wroble, Randall R.

AU - Watt, David S.

PY - 1976/8/1

Y1 - 1976/8/1

N2 - An effective sequence for the synthesis of α,β-unsaturated ketones involves (1) the Horner-Emmons modification of the Wittig reaction to synthesize α,β-unsaturated nitriles, R2CH2(R1)C=C(R3)CN, from carbonyl compounds, R2CH2COR1, and (2) the oxidative decyanation of the α,β-unsaturated nitriles to afford.ß-unsaturated ketones, R2CH=C(R1)COR3, by sequential treatment with lithium diisopropylamide, oxygen gas, sodium sulfite, and sodium hydroxide.

AB - An effective sequence for the synthesis of α,β-unsaturated ketones involves (1) the Horner-Emmons modification of the Wittig reaction to synthesize α,β-unsaturated nitriles, R2CH2(R1)C=C(R3)CN, from carbonyl compounds, R2CH2COR1, and (2) the oxidative decyanation of the α,β-unsaturated nitriles to afford.ß-unsaturated ketones, R2CH=C(R1)COR3, by sequential treatment with lithium diisopropylamide, oxygen gas, sodium sulfite, and sodium hydroxide.

UR - http://www.scopus.com/inward/record.url?scp=0346925658&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0346925658&partnerID=8YFLogxK

U2 - 10.1021/jo00879a037

DO - 10.1021/jo00879a037

M3 - Article

AN - SCOPUS:0346925658

VL - 41

SP - 2939

EP - 2940

IS - 17

ER -

A Synthesis of α,β-Unsaturated Ketones from α,β-Unsaturated Nitriles

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this