Abstract
Fourteen ketone/thione-stabilized triphenylphosphonium methylides were subjected to conventional gas-phase and flash vacuum pyrolysis (FVP). The kinetics of the first-order thermal gas-phase reactions of all these compounds were investigated over 360–653 K temperature range. The values of the Arrhenius log A and energy of activation of these ylides averaged 11.52 ± 0.34 s−1 and 133.20 ± 3.14 kJ mol−1, respectively. The products of sealed-tube (static) and FVP were analyzed and compared. A mechanism is proposed to account for the products of reaction. The rate constants [k (s−1)] of the substrates at 500 K were calculated and used to substantiate the proposed mechanism of pyrolysis, and to rationalize the thermal gas-phase reactivities of the ylides under study. Copyright © 2010 John Wiley & Sons, Ltd.
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