Kinetics studies of rapid strain-promoted [3 + 2]-cycloadditions of nitrones with biaryl-aza-cyclooctynone

Download
  1. Get@NRC: Kinetics studies of rapid strain-promoted [3 + 2]-cycloadditions of nitrones with biaryl-aza-cyclooctynone (Opens in a new window)
DOIResolve DOI: http://doi.org/10.1039/c2ob07165g
AuthorSearch for: ; Search for: ; Search for: ; Search for:
TypeArticle
Journal titleOrganic & Biomolecular Chemistry
ISSN1477-0520
1477-0539
Volume10
Issue15
Pages30663070
AbstractStrain-promoted cycloadditions of cyclic nitrones with biaryl-aza-cyclooctynone (BARAC) proceed with rate constants up to 47.3 M−¹ s−¹, this corresponds to a 47-fold rate enhancement relative to reaction of BARAC with benzyl azide and a 14-fold enhancement over previously reported strain promoted alkyne–nitrone cycloadditions (SPANC). Studies of the SPANC reaction using the linear free energy relationship defined by the Hammett equation demonstrated that the cycloaddition reaction has a rho value of 0.25 ± 0.04, indicating that reaction is not sensitive to substituents and thus should have broad applicability.
Publication date
LanguageEnglish
AffiliationNRC Steacie Institute for Molecular Sciences; National Research Council Canada
Peer reviewedYes
NPARC number21268961
Export citationExport as RIS
Report a correctionReport a correction
Record identifier7053dfee-adb0-4474-95fa-5d1be1b2f7bf
Record created2013-11-28
Record modified2016-05-09
Bookmark and share
  • Share this page with Facebook (Opens in a new window)
  • Share this page with Twitter (Opens in a new window)
  • Share this page with Google+ (Opens in a new window)
  • Share this page with Delicious (Opens in a new window)