Literature DB >> 29249841

Iodine-mediated rearrangements of diallylsilanes.

Gregory W O'Neil1, Elizabeth J Cummins1.   

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.

Entities:  

Keywords:  Amine annulation; Cross-metathesis; Diallylsilane; Rearrangement; Silacyclobutane

Year:  2017        PMID： 29249841      PMCID： PMC5730080          DOI： 10.1016/j.tetlet.2017.07.045

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  4 in total

1.  Direct conversion of β-hydroxyketones to cyclic disiloxanes.

Authors:  Gregory W O'Neil; Michael M Miller; Kyle P Carter
Journal:  Org Lett       Date:  2010-10-27       Impact factor: 6.005

2.  A qualitative examination of the effects of silicon substituents on the efficiency of cross-coupling reactions.

Authors:  Scott E Denmark; Luc Neuville; Matthew E L Christy; Steven A Tymonko
Journal:  J Org Chem       Date:  2006-10-27       Impact factor: 4.354

3.  Substituent effects on the reactivity of the silicon-carbon double bond.

Authors:  T L Morkin; W J Leigh
Journal:  Acc Chem Res       Date:  2001-02       Impact factor: 22.384

4.  Stereocontrolled synthesis of 1,3-diols from enones: cooperative Lewis base-mediated intramolecular carbonyl hydrosilylations.

Authors:  Casey Medina; Kyle P Carter; Michael Miller; Timothy B Clark; Gregory W O'Neil
Journal:  J Org Chem       Date:  2013-09-06       Impact factor: 4.354
  4 in total
  2 in total

1.  Chemoselective Carbonyl Allylations with Alkoxyallylsiletanes.

Authors:  Paul Spaltenstein; Elizabeth J Cummins; Kelly-Marie Yokuda; Tim Kowalczyk; Timothy B Clark; Gregory W O'Neil
Journal:  J Org Chem       Date:  2019-03-13       Impact factor: 4.354

2.  Sequential iodine-mediated diallylsilane rearrangement/asymmetric dihydroxylation: Synthesis and reactions of enantioenriched oxasilacycles.

Authors:  Christopher R Myers; Paul Spaltenstein; Lauren K Baker; Cody L Schwans; Timothy B Clark; Gregory W O'Neil
Journal:  Tetrahedron Lett       Date:  2021-09-08       Impact factor: 2.032
  2 in total

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