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Kinetics and mechanism of elimination of methoxyphenethyl chlorides in the gas phase

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Abstract

The kinetics for the gas phase elimination of o-and m-methoxy-2-phenylethyl chlorides have been investigated over the temperature range of 390-464°C and pressure range of 38–119 Torr. The reactions in seasoned vessels and in the presence of the free radical inhibitor propene, are homogeneous and unimolecular and follow a first-order rate law. The o-anisyl and p-anisyl substituents at the β-position of ethyl chloride assist anchimerically the elimination processes. The formation of a cyclic product, benzodihydrofuran, from o-methoxy-2-phenylethyl chloride suggests an intimate ion pair mechanism operating in this reaction.

Abstract

Кинетика газофазной элиминации о- и м-метокси-2-фенилэтил хлоридов исследована в интервале температур 390–464°C и при давлениях 38–119 торр. Реакция в высушенных сосудах и в присутствии свободно-радикального ингибитора, пропена, является гомогенной, мономолекулярной. о-Анизильные и п-анизильные заместители в β-положении этилхлорида анхимерически содействуют процессу элиминации. Образование циклического продукта, бензодигидрофурана, из о-метокси-2-фенилэтил хлорида свидетельствует о механизме, основанном на образовании интимной ионной пары.

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Authors and Affiliations

  1. Centro de Química, Instituto Venezolano de Investigaciones Científicas, Apartado 21827, 1020-A, Caracas, Venezuela

    R. M. Domînguez, A. Rotinov, J. A. Hernández, A. I. Martín, J. D. Medina & G. Chuchani

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  1. R. M. Domînguez
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  2. A. Rotinov
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  3. J. A. Hernández
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  4. A. I. Martín
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  5. J. D. Medina
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  6. G. Chuchani
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Domînguez, R.M., Rotinov, A., Hernández, J.A. et al. Kinetics and mechanism of elimination of methoxyphenethyl chlorides in the gas phase. React Kinet Catal Lett 33, 285–292 (1987). https://doi.org/10.1007/BF02128077

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  • DOI: https://doi.org/10.1007/BF02128077

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