Isotope effects for Lewis acid catalyzed Diels-Alder reactions. The experimental transition state Academic Article

abstract

• 2H and 13C kinetic isotope effects were determined for all positions on isoprene in its reactions with methyl vinyl ketone, ethyl acrylate, and acrolein catalyzed by Et2AlCl. The results are taken as supporting a highly asynchronous concerted [4+2] cycloaddition. Comparison of the experimental isotope effects with calculated values supports this conclusion and the accuracy of the calculated transition structure.

authors

• Singleton, Daniel

author list (cited authors)

• Singleton, D. A., Merrigan, S. R., Beno, B. R., & Houk, K. N.

citation count

• 28

publication date

• August 1999

publisher

• Elsevier BV  Publisher

published in

• Tetrahedron Letters  Journal

keywords

• Catalysis
• Diels-alder Reactions
• Isotope Effects
• Transition States

Digital Object Identifier (DOI)

• 10.1016/s0040-4039(99)01148-x

start page

• 5817

end page

• 5821

volume

• 40

issue

• 32