Work

Stereoelectronic Effects in the Fragmentation of γ-Silyloxy-β-hydroxy-α-diazocarbonyl Compounds

Year: 2012

Type: article

Abstract: A series of γ-silyloxy-β-hydroxy-α-diazocarbonyl compounds were prepared as fragmentation substrates to probe the hypothesis that steric interactions between the diazo ester and adjacent silyloxy group can play an important role in determining the success of fragmentations. Proper stereoelectronic alignment of the diazo ester and the departing hydroxyl group is necessary for productive fragmentation to occur.

Source: The Journal of Organic Chemistry

DOI: 10.1021/jo301944t

Authors: Nitinkumar D. Jabre, Matthias Brewer

Institution: University of Vermont

Language: English

Topic: Cyclopropane Reaction Mechanisms

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: National Institute of General Medical Sciences

Awards: G1497838195, G2949381749, G4202910764