Solvent-free Wittig olefination with stabilized phosphoranes - Scope and limitations

Thies Thiemann; Masataka Watanabe; Yasuko Tanaka; Shuntaro Mataka

doi:10.1039/b311894k

Solvent-free Wittig olefination with stabilized phosphoranes - Scope and limitations

Thies Thiemann, Masataka Watanabe, Yasuko Tanaka, Shuntaro Mataka

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

34 Citations (Scopus)

Abstract

Neat mixtures of arene/hetarenecarbaldehydes, alkanals as well as alkenals with alkyl (triphenylphosphoranylidene)acetates react exothermally to furnish the corresponding alkenes. In certain cases, heating has to be provided externally. Reaction times are short and yields are generally very high. Neat mixtures of ketones and alkyl (triphenylphosphoranylidene)acetates react preferentially under microwave irradiation. The better stabilized phosphoranes do not react in the solid state with aldehydes or ketones under conventional heating, but necessitate microwave irradiation, although not all of the phosphoranes have been found to be stable under microwave irradiation at 500 W (2450 MHz).

Original language	English
Pages (from-to)	578-584
Number of pages	7
Journal	New Journal of Chemistry
Volume	28
Issue number	5
DOIs	https://doi.org/10.1039/b311894k
Publication status	Published - May 2004
Externally published	Yes

ASJC Scopus subject areas

Catalysis
General Chemistry
Materials Chemistry

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abstract = "Neat mixtures of arene/hetarenecarbaldehydes, alkanals as well as alkenals with alkyl (triphenylphosphoranylidene)acetates react exothermally to furnish the corresponding alkenes. In certain cases, heating has to be provided externally. Reaction times are short and yields are generally very high. Neat mixtures of ketones and alkyl (triphenylphosphoranylidene)acetates react preferentially under microwave irradiation. The better stabilized phosphoranes do not react in the solid state with aldehydes or ketones under conventional heating, but necessitate microwave irradiation, although not all of the phosphoranes have been found to be stable under microwave irradiation at 500 W (2450 MHz).",

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T1 - Solvent-free Wittig olefination with stabilized phosphoranes - Scope and limitations

AU - Thiemann, Thies

AU - Watanabe, Masataka

AU - Tanaka, Yasuko

AU - Mataka, Shuntaro

PY - 2004/5

Y1 - 2004/5

N2 - Neat mixtures of arene/hetarenecarbaldehydes, alkanals as well as alkenals with alkyl (triphenylphosphoranylidene)acetates react exothermally to furnish the corresponding alkenes. In certain cases, heating has to be provided externally. Reaction times are short and yields are generally very high. Neat mixtures of ketones and alkyl (triphenylphosphoranylidene)acetates react preferentially under microwave irradiation. The better stabilized phosphoranes do not react in the solid state with aldehydes or ketones under conventional heating, but necessitate microwave irradiation, although not all of the phosphoranes have been found to be stable under microwave irradiation at 500 W (2450 MHz).

AB - Neat mixtures of arene/hetarenecarbaldehydes, alkanals as well as alkenals with alkyl (triphenylphosphoranylidene)acetates react exothermally to furnish the corresponding alkenes. In certain cases, heating has to be provided externally. Reaction times are short and yields are generally very high. Neat mixtures of ketones and alkyl (triphenylphosphoranylidene)acetates react preferentially under microwave irradiation. The better stabilized phosphoranes do not react in the solid state with aldehydes or ketones under conventional heating, but necessitate microwave irradiation, although not all of the phosphoranes have been found to be stable under microwave irradiation at 500 W (2450 MHz).

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Solvent-free Wittig olefination with stabilized phosphoranes - Scope and limitations

Abstract

ASJC Scopus subject areas

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