Bond Memory in Dynamically Determined Stereoselectivity Academic Article

abstract

• The carboborative ring contraction of cyclohexenes exhibits an abnormal selectivity pattern in which a formally concerted double migration gives rise to predominant but not exclusive inversion products. In dynamic trajectories, the inversion and retention products are formed from the same transition state, and the trajectories accurately account for the experimental product ratios. The unusual origin of the selectivity is the dynamically retained non-equivalence of newly formed versus pre-existing bonds after the first bond migration.

authors

• Singleton, Daniel

altmetric score

• 8.05

author list (cited authors)

• Roytman, V. A., Jin, S., Nguyen, V. T., Nguyen, V. D., Haug, G. C., Larionov, O. V., & Singleton, D. A.

citation count

• 7

complete list of authors

• Roytman, Vladislav A||Jin, Shengfei||Nguyen, Vu T||Nguyen, Viet D||Haug, Graham C||Larionov, Oleg V||Singleton, Daniel A

publication date

• January 2019

publisher

• American Chemical Society (ACS)  Publisher

published in

• Journal of the American Chemical Society  Journal

keywords

• Molecular Conformation
• Quantum Theory
• Stereoisomerism

PubMed Central ID

• 31852185

Digital Object Identifier (DOI)

• 10.1021/jacs.9b12227

start page

• 85

end page

• 88

volume

• 142

issue

• 1