Protonation-triggered Conformational Modulation of an N,N´‑Dialkylbispidine: First observation of the elusive boat-boat conformer
2013 (English)In: Organic and biomolecular chemistry, ISSN 1477-0520, E-ISSN 1477-0539, Vol. 11, 6292-6299 p.Article in journal (Refereed) Published
Modulation of the solution conformations of N,N′-bis(benzhydryl)bispidine has been achieved by protonation. Conformers have been characterized by NMR spectroscopy using nuclear Overhauser effects and residual dipolar couplings. In contrast to the preference for the chair–chair conformation for the free base and the monoprotonated species, the diprotonated bispidine is revealed to exist as a mixture of chair–boat and boat–boat conformers. While boat–boat conformers of bispidines have previously not been detected, they are here observed to constitute up to 70% of the bispidine population.
Place, publisher, year, edition, pages
2013. Vol. 11, 6292-6299 p.
Natural Sciences Organic Chemistry
Research subject Organic Chemistry
IdentifiersURN: urn:nbn:se:uu:diva-206042DOI: 10.1039/c3ob41122bISI: 000324507100010OAI: oai:DiVA.org:uu-206042DiVA: diva2:643295
FunderSwedish Research Council