Water as efficient medium for mild decarbonylation of tertiary aldehydes

Carlos Jose Romao

doi:10.1016/j.tetlet.2011.03.012

Water as efficient medium for mild decarbonylation of tertiary aldehydes

Carlos Jose Romao

Instituto de Tecnologia Química e Biológica António Xavier (ITQB)

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

9 Citations (Scopus)

Abstract

Decarbonylation of the tertiary aldehydes 4-ethyl-4-formyl-hexanenitrile (2) and 2-methyl-2-phenylpropanal (4) promoted by dioxygen occurs at room temperature only if suspended in water probably via the sequential acyl radical-CO liberation-tertiary radical that is promoted by an 'on water' process originating preferentially from the corresponding tertiary hydroperoxide.

Original language	Unknown
Pages (from-to)	2803-2807
Journal	Tetrahedron Letters
Volume	52
Issue number	22
DOIs	https://doi.org/10.1016/j.tetlet.2011.03.012
Publication status	Published - 1 Jan 2011

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10.1016/j.tetlet.2011.03.012

Cite this

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title = "Water as efficient medium for mild decarbonylation of tertiary aldehydes",

abstract = "Decarbonylation of the tertiary aldehydes 4-ethyl-4-formyl-hexanenitrile (2) and 2-methyl-2-phenylpropanal (4) promoted by dioxygen occurs at room temperature only if suspended in water probably via the sequential acyl radical-CO liberation-tertiary radical that is promoted by an 'on water' process originating preferentially from the corresponding tertiary hydroperoxide.",

keywords = "KINETICS, ALKYL, MECHANISM, PHENYLACETYL, ADDITION-REACTIONS, UNSYMMETRICAL KETONES, CATALYSIS, ACYL RADICAL CYCLIZATION, CARBON-MONOXIDE, CHEMISTRY",

author = "Romao, {Carlos Jose}",

year = "2011",

month = jan,

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doi = "10.1016/j.tetlet.2011.03.012",

language = "Unknown",

volume = "52",

pages = "2803--2807",

journal = "Tetrahedron Letters",

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publisher = "Elsevier Science B.V., Amsterdam.",

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TY - JOUR

T1 - Water as efficient medium for mild decarbonylation of tertiary aldehydes

AU - Romao, Carlos Jose

PY - 2011/1/1

Y1 - 2011/1/1

N2 - Decarbonylation of the tertiary aldehydes 4-ethyl-4-formyl-hexanenitrile (2) and 2-methyl-2-phenylpropanal (4) promoted by dioxygen occurs at room temperature only if suspended in water probably via the sequential acyl radical-CO liberation-tertiary radical that is promoted by an 'on water' process originating preferentially from the corresponding tertiary hydroperoxide.

AB - Decarbonylation of the tertiary aldehydes 4-ethyl-4-formyl-hexanenitrile (2) and 2-methyl-2-phenylpropanal (4) promoted by dioxygen occurs at room temperature only if suspended in water probably via the sequential acyl radical-CO liberation-tertiary radical that is promoted by an 'on water' process originating preferentially from the corresponding tertiary hydroperoxide.

KW - KINETICS

KW - ALKYL

KW - MECHANISM

KW - PHENYLACETYL

KW - ADDITION-REACTIONS

KW - UNSYMMETRICAL KETONES

KW - CATALYSIS

KW - ACYL RADICAL CYCLIZATION

KW - CARBON-MONOXIDE

KW - CHEMISTRY

U2 - 10.1016/j.tetlet.2011.03.012

DO - 10.1016/j.tetlet.2011.03.012

M3 - Article

VL - 52

SP - 2803

EP - 2807

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 22

ER -