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

published proceedings

• TETRAHEDRON LETTERS

author list (cited authors)

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

citation count

• 32

complete list of authors

• Singleton, DA||Merrigan, SR||Beno, BR||Houk, KN

publication date

• January 1, 1999 11:11 AM

publisher

• Elsevier  Publisher
• Elsevier BV  Publisher

published in

• Tetrahedron Letters: the international journal for the rapid publication of all preliminary communications in organic chemistry  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

issue

• 32