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Homolytic 1,2-rearrangement of pinacolone mercaptoles

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Summary

  1. 1.

    An investigation was made of the homolytic 1,2-rearrangement of pinacolone dibutyl, diphenyl, and butyl phenyl mercaptoles. In presence of t-butyl peroxide these mercaptoles are isomerized into the corresponding 1,2-bisalkylthio compounds, and the butyl phenyl mercaptole rearranges with predominant migration of the phenylthio group.

  2. 2.

    These mercaptoles are isomerized to some extent in absence of the peroxide by thermal cleavage at 130–140°.

  3. 3.

    The mechanism of the rearrangement of mercaptoles in absence of initiator was examined. It suggested that mercaptoles be divided into two groups depending on the stability of their C-S bonds.

  4. 4.

    The possibility of the rearrangement of mercaptoles by an intermolecular mechanism was studied. The rearrangement of a mercaptole into a mercaptal was effected in presence of t-butyl peroxide and dry hydrogen chloride.

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Literature cited

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    E. P. Gracheva, V. I. Laba, and M. F. Shostakovskii, Zh. obshch. khimii,33, 2501 (1963).

  2. 2.

    M. F. Shostakovskii, N. K. Kul'bovskaya, E. P. Gracheva, V. I. Laba, and L. M. Yakushina, Zh. obshch. khimii,32, 709 (1962).

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    E. P. Gracheva, V. I. Laba, N. K. Kul'bovskaya, and M. F. Shostakovskii, Zh. obshch. khimii,33, 2493 (1963).

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Additional information

This article is published in accordance with a resolution of the Conference of Chief Editors of Journals of the Academy of Sciences of the USSR, July 12, 1962, as a dissertation paper by V. I. Laba.

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Laba, V.I., Gracheva, E.P. Homolytic 1,2-rearrangement of pinacolone mercaptoles. Russ Chem Bull 13, 508–513 (1964). https://doi.org/10.1007/BF00844171

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Keywords

  • Hydrogen
  • Chloride
  • Migration
  • Peroxide
  • Phenyl