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Iodine-mediated rearrangements of diallylsilanes.

ABSTRACT: Diallylsilanes can be made to rearrange upon treatment with I2. Of the silanes tested, diallyldiphenylsilane showed the greatest propensity to undergo this intramolecular carbocation allylation process. After etherification of the initially formed iodosilane, the products from this transformation represent useful synthetic intermediates, suitable for alkylation and cross-metathesis/annulation reactions.

SUBMITTER: O'Neil GW

PROVIDER: S-EPMC5730080 | biostudies-literature | 2017 Aug

REPOSITORIES: biostudies-literature

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Iodine-mediated rearrangements of diallylsilanes.

O'Neil Gregory W GW Cummins Elizabeth J EJ

Tetrahedron letters 20170711 35

Diallylsilanes can be made to rearrange upon treatment with I<sub>2</sub>. Of the silanes tested, diallyldiphenylsilane showed the greatest propensity to undergo this intramolecular carbocation allylation process. After etherification of the initially formed iodosilane, the products from this transformation represent useful synthetic intermediates, suitable for alkylation and cross-metathesis/annulation reactions. ...[more]

PMID: 29249841

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