Nucleophilic substitution reaction of 5-t-butyl-2-methoxy-3H-azepine with alkoxides and alkyllithium reagents: A formation of bis(5-t-butyl-3H-azepin-2-yl)-methane having a vinamidine conjugation

Kyosuke Satake, Yasuhiro Kubota, Hideki Okamoto, Masaru Kimura

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

Reaction of 5-t-butyl-2-methoxy-3H-azepine (2) with nuclephiles (alkoxides or t-butyllithium) gave respective substitution product at 2-position of the ring. Unexpectedly, when methyllithium was used as a nucleophile, bis(5-t-butyl-3H-azepin-2-yl)methane (7), the structure of which found to be tautomeric vinamidine (7a,b), was formed. Tautomerization between 7 and 7a,b was characterized spectroscopically and theoretically based on the levels of B3LYP/6-31G(d).

Original languageEnglish
Pages (from-to)223-228
Number of pages6
JournalHeterocycles
Volume57
Issue number2
DOIs
Publication statusPublished - Feb 1 2002

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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