Iodine Mediated Rearrangement of Diphenyldiallyl Silane
Research Mentor(s)
O'Neil, Gregory (Gregory W.)
Description
The iodine-mediated rearrangement of diallyldiphenyl silane yielded a stereocenter at the site of a new carbon-carbon bond. In an attempt to isolate the enantiomers, the racemic mixture underwent a Sharpless Asymmetric Dihydoxilation and intramolecular ring closure to create two distinct diastereomers. Separation of the diastereomers was achieved using column chromatography on silica. The stereochemistry of the two compounds was identified by using COSy and NOESy techniques. This structure is a versatile precursor for the synthesis of various natural products.
Document Type
Event
Start Date
17-5-2018 12:00 AM
End Date
17-5-2018 12:00 AM
Department
Chemistry
Genre/Form
student projects, posters
Subjects – Topical (LCSH)
Organic compounds--Synthesis; Iodine compounds
Type
Image
Rights
Copying of this document in whole or in part is allowable only for scholarly purposes. It is understood, however, that any copying or publication of this document for commercial purposes, or for financial gain, shall not be allowed without the author’s written permission.
Language
English
Format
application/pdf
Iodine Mediated Rearrangement of Diphenyldiallyl Silane
The iodine-mediated rearrangement of diallyldiphenyl silane yielded a stereocenter at the site of a new carbon-carbon bond. In an attempt to isolate the enantiomers, the racemic mixture underwent a Sharpless Asymmetric Dihydoxilation and intramolecular ring closure to create two distinct diastereomers. Separation of the diastereomers was achieved using column chromatography on silica. The stereochemistry of the two compounds was identified by using COSy and NOESy techniques. This structure is a versatile precursor for the synthesis of various natural products.