A general synthesis of N-vinyl nitrones.

A general synthesis of N-vinyl nitrones. Research Abstract Details 

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A general synthesis of N-vinyl nitrones. Abstract Text:

Scott E Denmark,Justin I Montgomery,

A general synthesis of a new type of heterodiene, the N-vinyl nitrone, is described. The synthetic sequence begins with the conjugate addition of benzeneselenol to nitroalkenes (in turn derived from Henry reaction of an aldehyde and a nitroalkane) to provide 2-selenenylnitroalkenes. These selenonitroalkanes are reduced to the corresponding hydroxylamines which are combined with aldehydes to form nitrones. The phenylselenenyl-containing nitrones are then oxidized to selenoxides which undergo syn-selenoxide elimination to provide N-vinyl nitrones. Three X-ray crystal structures of substituted N-vinyl nitrones were obtained. In addition, the first [4+2] cycloaddition of an N-vinyl nitrone is reported.

A general synthesis of N-vinyl nitrones. Publishing Authors By Initials

SE Denmark,JI Montgomery,

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A general synthesis of N-vinyl nitrones. Journal Published:

PUBLICATION TYPE: Research Support, Non-U.S. Gov

Journal: The Journal of organic chemistry

VOLUME: 71

Page Numbers: 6211-20

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ISSN: 0022-3263

DAY: 4

MONTH: Aug

YEAR: 2006

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LANGUAGE: eng

NlmUniqueID: 2985193

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Grant and Affiliation Information for A general synthesis of N-vinyl nitrones.

AFFILIATION: Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801, USA.

Country: United States

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MEDLINETA: J Org Chem

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