ω-Bromoalkapolyenylmethyl ketones-I. Reaction of 5-bromo-3-penten-2-one with triphenylphosphine

J. Font; P. De March

doi:10.1016/S0040-4020(01)88895-5

ω-Bromoalkapolyenylmethyl ketones-I. Reaction of 5-bromo-3-penten-2-one with triphenylphosphine

J. Font, P. De March

Department of Chemistry

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

19 Citations (Scopus)

Abstract

The reaction of (E)-5-bromo-3-penten-2-one with triphenylphosphine affords a 3:1 mixture of two protomeric phosphonium salts 4-oxo 2 pentenyltriphenylphosphonium bromide and 4-oxo-1-pentenyltriphenyl-phosphonium bromide, characterized by the 13C NMR spectrum of the mixture. However, the common phosphorane of these salts gives two condensation products with benzaldehyde, corresponding to α- and γ-condensation respectively. © 1981.

Original language	English
Pages (from-to)	2391-2396
Journal	Tetrahedron
Volume	37
Issue number	13
DOIs	https://doi.org/10.1016/S0040-4020(01)88895-5
Publication status	Published - 1 Jan 1981

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abstract = "The reaction of (E)-5-bromo-3-penten-2-one with triphenylphosphine affords a 3:1 mixture of two protomeric phosphonium salts 4-oxo 2 pentenyltriphenylphosphonium bromide and 4-oxo-1-pentenyltriphenyl-phosphonium bromide, characterized by the 13C NMR spectrum of the mixture. However, the common phosphorane of these salts gives two condensation products with benzaldehyde, corresponding to α- and γ-condensation respectively. {\textcopyright} 1981.",

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AU - De March, P.

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Y1 - 1981/1/1

N2 - The reaction of (E)-5-bromo-3-penten-2-one with triphenylphosphine affords a 3:1 mixture of two protomeric phosphonium salts 4-oxo 2 pentenyltriphenylphosphonium bromide and 4-oxo-1-pentenyltriphenyl-phosphonium bromide, characterized by the 13C NMR spectrum of the mixture. However, the common phosphorane of these salts gives two condensation products with benzaldehyde, corresponding to α- and γ-condensation respectively. © 1981.

AB - The reaction of (E)-5-bromo-3-penten-2-one with triphenylphosphine affords a 3:1 mixture of two protomeric phosphonium salts 4-oxo 2 pentenyltriphenylphosphonium bromide and 4-oxo-1-pentenyltriphenyl-phosphonium bromide, characterized by the 13C NMR spectrum of the mixture. However, the common phosphorane of these salts gives two condensation products with benzaldehyde, corresponding to α- and γ-condensation respectively. © 1981.

U2 - 10.1016/S0040-4020(01)88895-5

DO - 10.1016/S0040-4020(01)88895-5

M3 - Article

VL - 37

SP - 2391

EP - 2396

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

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