Restricted rotation involving the tetrahedral carbon-VI. Some Diels-Alder adducts derived from 2-t-butylfuran

M. Nakamura, M. Oki, H. Nakanishi

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

1 - t - Butyl - 1,4 - dihydronaphthalene 1,4 - endoxide derivatives were prepared by treating 2 -t- butylfuran with some benzynes to see the effect of the bulkiness on the barrier to rotation. The NMR signals of the t-Bu group of these compounds split at low temperature, showing that the rotation about the CBu-C1 bond was frozen on the NMR time scale. Activation parameters for rotation were obtained by the total line shape analysis. On further lowering of the temperature, the restricted rotation of the Me in t-Bu group was observed. The signals of the Me groups were assigned by taking the chemical shifts and the through-space H-F couplings into consideration.

Original languageEnglish
Pages (from-to)543-548
Number of pages6
JournalTetrahedron
Volume30
Issue number4
DOIs
Publication statusPublished - 1974

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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