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A cascade thermal isomerisation of cyclobutane di-(carbomethoxy) Δ2-1,2,3-triazolines with intramolecular 1,3-dipolar cycloreversion as the key step

journal contribution
posted on 06.12.2017, 00:00 by D Margetic, Ronald WarrenerRonald Warrener, Douglas ButlerDouglas Butler, Chuan-Ming JinChuan-Ming Jin
Unprecedented thermal isomerisation of the strained ∆2-1,2,3-triazolines led to the formation of products possessing a novel 1,2,7-triaza-[3.3.0]octa-2-ene ring system incorporated in a norbornane framework. Experimental evidence and quantum chemical calculations have been used to support a postulated reaction mechanism involving as the first step, a rare example of intramolecular 1,3-dipolar cyclo-reversion. Subsequently, several steps involving 1,3-dipolar ring closure, hydrogen shifts and an intramolecular addition are postulated leading to the observed product of this deep-seated isomerisation. The influence of changing substituents on the product outcome of this novel reaction cascade was also studied.

Funding

Category 1 - Australian Competitive Grants (this includes ARC, NHMRC)

History

Volume

68

Issue

16

Start Page

3306

End Page

3318

Number of Pages

13

eISSN

1464-5416

ISSN

0040-4020

Location

United Kingdom

Publisher

Pergamon

Language

en-aus

Peer Reviewed

Yes

Open Access

No

Era Eligible

Yes

Journal

Tetrahedron.