Welcome to the new version of CaltechAUTHORS. Login is currently restricted to library staff. If you notice any issues, please email coda@library.caltech.edu
Published May 15, 2013 | Supplemental Material
Journal Article Open

α-Diazo-β-ketonitriles: Uniquely Reactive Substrates for Arene and Alkene Cyclopropanation

Abstract

An investigation of the intramolecular cyclopropanation reactions of α-diazo-β-ketonitriles is reported. These studies reveal that α-diazo-β-ketonitriles exhibit unique reactivity in their ability to undergo arene cyclopropanation reactions; other similar acceptor–acceptor-substituted diazo substrates instead produce mixtures of C–H insertion and dimerization products. α-Diazo-β-ketonitriles also undergo highly efficient intramolecular cyclopropanation of tri- and tetrasubstituted alkenes. In addition, the α-cyano-α-ketocyclopropane products are demonstrated to serve as substrates for S_(N)2, S_(N)2′, and aldehyde cycloaddition reactions.

Additional Information

© 2013 American Chemical Society. Received: February 21, 2013; Published: May 3, 2013. We thank Prof. Brian Stoltz, Dr. Scott Virgil, and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment. We also thank Sigma-Aldrich for a kind donation of chemicals. S.E.R. is a fellow of the Alfred P. Sloan Foundation and a Camille Dreyfus Teacher-Scholar. Financial support from the National Science Foundation (CAREER-1057143), Boehringer-Ingleheim, Amgen, and the California Institute of Technology is gratefully acknowledged.

Attached Files

Supplemental Material - ja401610p_si_001.pdf

Supplemental Material - ja401610p_si_002.pdf

Files

ja401610p_si_001.pdf
Files (17.0 MB)
Name Size Download all
md5:1851c7b14829f552144ab6c17e3db2a8
2.0 MB Preview Download
md5:3368d6ab8000b81a9d928fbc84a9163f
14.9 MB Preview Download

Additional details

Created:
August 19, 2023
Modified:
October 24, 2023