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

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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

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Organic Chemistry

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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.",

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year = "1976",

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doi = "10.1021/jo00879a037",

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

AU - Wroble, Randall R.

AU - Watt, David S.

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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.

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

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

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