Generation of ketenes from carboxylic acids using the mukaiyama reagent (1-methyl-2-chloropyridinium iodide)

Raymond L. Funk; Matthew M. Abelman; Kay M. Jellison

doi:10.1055/s-1989-34706

Generation of ketenes from carboxylic acids using the mukaiyama reagent (1-methyl-2-chloropyridinium iodide)

Raymond L. Funk
, Matthew M. Abelman
, Kay M. Jellison

Chemistry

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

47 Scopus citations

Abstract

Ketenes can be generated by treatment of carboxylic acids with l-methyl-2-chloropyridinium iodide and triethylamine and may be intermediates during macrolactonization reactions via the Mukaiyama procedure. A new procedure for the direct conversion of enoic acids to [2+2] ketene-olefin cydoadducts is described.

Original language	English (US)
Pages (from-to)	36-37
Number of pages	2
Journal	Synlett
Volume	1989
Issue number	1
DOIs	https://doi.org/10.1055/s-1989-34706
State	Published - Sep 1989

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1055/s-1989-34706

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title = "Generation of ketenes from carboxylic acids using the mukaiyama reagent (1-methyl-2-chloropyridinium iodide)",

abstract = "Ketenes can be generated by treatment of carboxylic acids with l-methyl-2-chloropyridinium iodide and triethylamine and may be intermediates during macrolactonization reactions via the Mukaiyama procedure. A new procedure for the direct conversion of enoic acids to [2+2] ketene-olefin cydoadducts is described.",

author = "Funk, \{Raymond L.\} and Abelman, \{Matthew M.\} and Jellison, \{Kay M.\}",

note = "Funding Information: We appreciate the financial support provided by the National Institutes of Health (Grant GM2-28663), Eli Lilly and Company, and the Alfred P. Sloan Foundation. High-field (360 MHz)1H and 13C NMR spectra were obtained on a spectrometer purchased with funds provided, in part, by the National Science Foundation (Grant CHE-80-24328). Mass spectra were obtained through the National Science Foundation Regional Mass Spectroscopy Center at the University of Nebraska (Grant CHE-82-11164). Publisher Copyright: {\textcopyright} 1989 Georg Thieme Verlag. All rights reserved.",

year = "1989",

month = sep,

doi = "10.1055/s-1989-34706",

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T1 - Generation of ketenes from carboxylic acids using the mukaiyama reagent (1-methyl-2-chloropyridinium iodide)

AU - Funk, Raymond L.

AU - Abelman, Matthew M.

AU - Jellison, Kay M.

N1 - Funding Information: We appreciate the financial support provided by the National Institutes of Health (Grant GM2-28663), Eli Lilly and Company, and the Alfred P. Sloan Foundation. High-field (360 MHz)1H and 13C NMR spectra were obtained on a spectrometer purchased with funds provided, in part, by the National Science Foundation (Grant CHE-80-24328). Mass spectra were obtained through the National Science Foundation Regional Mass Spectroscopy Center at the University of Nebraska (Grant CHE-82-11164). Publisher Copyright: © 1989 Georg Thieme Verlag. All rights reserved.

PY - 1989/9

Y1 - 1989/9

N2 - Ketenes can be generated by treatment of carboxylic acids with l-methyl-2-chloropyridinium iodide and triethylamine and may be intermediates during macrolactonization reactions via the Mukaiyama procedure. A new procedure for the direct conversion of enoic acids to [2+2] ketene-olefin cydoadducts is described.

AB - Ketenes can be generated by treatment of carboxylic acids with l-methyl-2-chloropyridinium iodide and triethylamine and may be intermediates during macrolactonization reactions via the Mukaiyama procedure. A new procedure for the direct conversion of enoic acids to [2+2] ketene-olefin cydoadducts is described.

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DO - 10.1055/s-1989-34706

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AN - SCOPUS:85023361751

SN - 0936-5214

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JO - Synlett

JF - Synlett

IS - 1

ER -

Generation of ketenes from carboxylic acids using the mukaiyama reagent (1-methyl-2-chloropyridinium iodide)

Abstract

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