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Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
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From furans to phosphinines.

Yanli Mao1, Francois Mathey

  • 1Division of Chemistry & Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371.

Organic Letters
|July 1, 2010
PubMed
Summary
This summary is machine-generated.

Researchers reacted methylenechlorophosphine-pentacarbonyltungsten with furan, forming a [4 + 2] adduct. Subsequent BBr(3) treatment and two steps yielded a 2-alkoxyphosphinine.

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Area of Science:

  • Organometallic Chemistry
  • Organic Synthesis
  • Heterocyclic Chemistry

Background:

  • Phosphorus-containing heterocycles are valuable synthetic intermediates.
  • Tungsten-based organometallic complexes offer unique reactivity.
  • Furan serves as a diene in cycloaddition reactions.

Purpose of the Study:

  • To investigate the reactivity of methylenechlorophosphine-pentacarbonyltungsten with furan.
  • To synthesize novel phosphorus-containing heterocyclic compounds.
  • To explore the utility of boron tribromide in adduct modification.

Main Methods:

  • Diels-Alder reaction between a tungsten-phosphine complex and furan.
  • Lewis acid-mediated cleavage of the oxygen bridge using boron tribromide.
  • Subsequent synthetic transformations to yield the final product.

Main Results:

  • Formation of a [4 + 2] cycloadduct between methylenechlorophosphine-pentacarbonyltungsten and furan.
  • Successful cleavage of the adduct's oxygen bridge with BBr(3).
  • Synthesis of a 2-alkoxyphosphinine derivative through a multi-step process.

Conclusions:

  • Methylenechlorophosphine-pentacarbonyltungsten can participate in cycloaddition reactions with furan.
  • Boron tribromide is effective for cleaving the oxygen bridge in the adduct.
  • A novel route to 2-alkoxyphosphinines has been established.