Oxidative cycloaddition of thiophenophanes - [n](2.5)parathiophenophane (n = 8,10-12,14), [8](2,4)metathiophenophane and [2.2](2,5)parametathiophenophane

Yuan Qiang Li, Thies Thiemann, Keisuke Mimura, Tsuyoshi Sawada, Shuntaro Mataka, Masashi Tashiro

Research output: Contribution to journalArticlepeer-review

14 Citations (Scopus)

Abstract

The oxidative cycloaddition of 3,4-dibromo-[n](2,5)thiophenophanes 12b-e and (2,4)[8]thiophenophane 16 with dienophiles gave stereoselectively O=S-bridged cycloadducts 18, 19 and 24. The X-ray analysis of cycloadduct 18a shows it to have a rigid conformation. The molecules can be regarded as a new series of paddlanes. Under the same oxidative conditions, 3,4-dibromo-[8](2,5)thiophenophane (12a) gave the two dimers 29 and 30. The results of the X-ray analysis of 29 are discussed.

Original languageEnglish
Pages (from-to)1841-1850
Number of pages10
JournalEuropean Journal of Organic Chemistry
Issue number9
DOIs
Publication statusPublished - Sep 1998
Externally publishedYes

Keywords

  • Oxidative Diels-Alder reaction
  • Thiophenophane S-monoxide
  • Thiophenophanes

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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