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An ene reaction with a polar transition state as ascertained from solvent effects
Author(s) -
Laszlo Pierre,
TestonHenry Michelle
Publication year - 1991
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.610041004
Subject(s) - chemistry , ene reaction , polar , reaction rate constant , polarity (international relations) , solvent , chloride , acrylate , catalysis , methyl acrylate , aluminium chloride , transition state , photochemistry , organic chemistry , computational chemistry , aluminium , kinetics , copolymer , polymer , biochemistry , physics , quantum mechanics , astronomy , cell
Abstract A kinetic study is reported for the ene reaction between methyl acrylate as the enophile and β‐pinene, with aluminium chloride as catalyst, in a series of solvents varying in polarity. These experiments point to a transition state having pronounced zwitterionic character, in line with earlier suggestions in the literature. An unexpected and significant change of the rate constant with the initial concentrations is also found.