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Literature DB >> 11841256

An unexpected bispericyclic transition structure leading to 4+2 and 2+4 cycloadducts in the endo dimerization of cyclopentadiene.

Pierluigi Caramella¹, Paolo Quadrelli, Lucio Toma.

Abstract

The stereospecific endo dimerization of cyclopentadiene takes place through an asynchronous and symmetrical bispericyclic transition structure, which shows a merging of the 4+2 and 2+4 cycloaddition paths. The shape of the transition structure testifies to the presence of attractive Salem/Houk secondary orbital interactions assisting the endo approach.

Entities: Chemical

Year: 2002 PMID： 11841256 DOI： 10.1021/ja016622h

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

20 in total

1. Dynamic effects on the periselectivity, rate, isotope effects, and mechanism of cycloadditions of ketenes with cyclopentadiene.

Authors: Bryson R Ussing; Chao Hang; Daniel A Singleton
Journal: J Am Chem Soc Date: 2006-06-14 Impact factor: 15.419

Review 2. Bifurcations on potential energy surfaces of organic reactions.

Authors: Daniel H Ess; Steven E Wheeler; Robert G Iafe; Lai Xu; Nihan Celebi-Olçüm; Kendall N Houk
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

3. Dynamically Complex [6+4] and [4+2] Cycloadditions in the Biosynthesis of Spinosyn A.

Authors: Ashay Patel; Zhuo Chen; Zhongyue Yang; Osvaldo Gutiérrez; Hung-wen Liu; K N Houk; Daniel A Singleton
Journal: J Am Chem Soc Date: 2016-03-09 Impact factor: 15.419

Review 4. Natural [4 + 2]-Cyclases.

Authors: Byung-Sun Jeon; Shao-An Wang; Mark W Ruszczycky; Hung-Wen Liu
Journal: Chem Rev Date: 2016-12-01 Impact factor: 60.622

An unexpected bispericyclic transition structure leading to 4+2 and 2+4 cycloadducts in the endo dimerization of cyclopentadiene.

1. Dynamic effects on the periselectivity, rate, isotope effects, and mechanism of cycloadditions of ketenes with cyclopentadiene.

Review 2. Bifurcations on potential energy surfaces of organic reactions.

3. Dynamically Complex [6+4] and [4+2] Cycloadditions in the Biosynthesis of Spinosyn A.

Review 4. Natural [4 + 2]-Cyclases.

5. Racing carbon atoms. Atomic motion reaction coordinates and structural effects on Newtonian kinetic isotope effects.

Review 6. The expanding world of biosynthetic pericyclases: cooperation of experiment and theory for discovery.

7. Dynamic origin of the stereoselectivity of a nucleophilic substitution reaction.

8. Recrossing and dynamic matching effects on selectivity in a Diels-Alder reaction.

9. Control elements in dynamically determined selectivity on a bifurcating surface.

10. Newtonian kinetic isotope effects. Observation, prediction, and origin of heavy-atom dynamic isotope effects.