1,3-Dipolar Cycloaddition Reaction of Substituted Trimethylstannylacetylenes with Nitrile Oxides

Takao Sakamoto, Daishi Uchiyama, Yoshinori Kondo, Hiroshi Yamanaka

Research output: Contribution to journalArticlepeer-review

19 Citations (Scopus)

Abstract

1,3-Dipolar cycloaddition reaction of trimethylstannylacetylene with nitrile oxides yielded 3-substituted 5-(trimethylstannyl)isoxazoles. On the other hand, the same reaction of (trimethylstannyl)phenylacetylene, -1-hexyne, and -(trimethylsilyl)acetylene gave 3,5-disubstituted 4-(trimethylstannyl)isoxazoles almost regioselectively. The regioselectivity of the cycloaddition reaction is interpreted by application of the frontier-electron theory.

Original languageEnglish
Pages (from-to)478-480
Number of pages3
JournalChemical and Pharmaceutical Bulletin
Volume41
Issue number3
DOIs
Publication statusPublished - 1993

Keywords

  • 1,3-dipolar cycloaddition
  • MO calculation
  • nitrile oxide
  • regioselectivity
  • trimethylstannylacetylene
  • trimethylstannylisoxazole

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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