Skip to main content
Journal cover image

Origins of Stereoselectivity in Radical Additions: Reactions of Alkenes and Radicals Bearing Oxazolidine and Thiazolidine Amide Groups

Publication ,  Journal Article
Porter, NA; Rosenstein, IJ; Breyer, RA; Bruhnke, JD; Wu, WX; McPhail, AT
Published in: Journal of the American Chemical Society
September 1, 1992

Single-crystal X-ray analysis of four alkenes that undergo stereoselective radical addition reactions are reported. The facial selectivity of radical additions to these alkenes is understood based upon their solid-state conformations. Alkenes which have a conformation placing a group at a position in space sterically protecting one of the faces from addition undergo radical addition with diastereofacial selectivity. The structures of the alkenes are analyzed by the polar coordinates of groups relative to the alkene center undergoing addition. The analysis of conformations of alkenes also provides a rationale for stereoselectivity in the reactions of radicals derived from the alkenes. Factors which influence the conformation of the alkene also apparently influence the conformation of analogous radicals. Several products of addition were also subjected to X-ray crystallographic analysis, and the steric factors which influence the conformation of the reactant alkene are also observed to affect the conformation of the radical addition products. © 1992, American Chemical Society. All rights reserved.

Duke Scholars

Published In

Journal of the American Chemical Society

DOI

EISSN

1520-5126

ISSN

0002-7863

Publication Date

September 1, 1992

Volume

114

Issue

20

Start / End Page

7664 / 7676

Related Subject Headings

  • General Chemistry
  • 40 Engineering
  • 34 Chemical sciences
  • 03 Chemical Sciences
 

Citation

APA
Chicago
ICMJE
MLA
NLM
Porter, N. A., Rosenstein, I. J., Breyer, R. A., Bruhnke, J. D., Wu, W. X., & McPhail, A. T. (1992). Origins of Stereoselectivity in Radical Additions: Reactions of Alkenes and Radicals Bearing Oxazolidine and Thiazolidine Amide Groups. Journal of the American Chemical Society, 114(20), 7664–7676. https://doi.org/10.1021/ja00046a010
Porter, N. A., I. J. Rosenstein, R. A. Breyer, J. D. Bruhnke, W. X. Wu, and A. T. McPhail. “Origins of Stereoselectivity in Radical Additions: Reactions of Alkenes and Radicals Bearing Oxazolidine and Thiazolidine Amide Groups.” Journal of the American Chemical Society 114, no. 20 (September 1, 1992): 7664–76. https://doi.org/10.1021/ja00046a010.
Porter NA, Rosenstein IJ, Breyer RA, Bruhnke JD, Wu WX, McPhail AT. Origins of Stereoselectivity in Radical Additions: Reactions of Alkenes and Radicals Bearing Oxazolidine and Thiazolidine Amide Groups. Journal of the American Chemical Society. 1992 Sep 1;114(20):7664–76.
Porter, N. A., et al. “Origins of Stereoselectivity in Radical Additions: Reactions of Alkenes and Radicals Bearing Oxazolidine and Thiazolidine Amide Groups.” Journal of the American Chemical Society, vol. 114, no. 20, Sept. 1992, pp. 7664–76. Scopus, doi:10.1021/ja00046a010.
Porter NA, Rosenstein IJ, Breyer RA, Bruhnke JD, Wu WX, McPhail AT. Origins of Stereoselectivity in Radical Additions: Reactions of Alkenes and Radicals Bearing Oxazolidine and Thiazolidine Amide Groups. Journal of the American Chemical Society. 1992 Sep 1;114(20):7664–7676.
Journal cover image

Published In

Journal of the American Chemical Society

DOI

EISSN

1520-5126

ISSN

0002-7863

Publication Date

September 1, 1992

Volume

114

Issue

20

Start / End Page

7664 / 7676

Related Subject Headings

  • General Chemistry
  • 40 Engineering
  • 34 Chemical sciences
  • 03 Chemical Sciences