Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact:

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

Communication | Regular issue | Vol 57, No. 2, 2002, pp.223-228
Published online, 1st January, 1970
DOI: 10.3987/COM-01-9397
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, and Masaru Kimura

*Department of Chemistry, Faculty of Science, Okayama University, 3-1-1 Tsushima-naka, Okayama 700-8530, Japan


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).