A Simple Method for the Visualization of Chair and Twist-Boat Transition States in Torsionally Controlled Addition Reactions

作者：Niederer Kyle A; Fodor Matthew D; Catino Arthur J^*

来源：Journal of Chemical Education, 2018, 95(7): 1230-1234.

DOI：10.1021/acs.jchemed.8b00055

• Graduate Education/Research
• Upper-Division Undergraduate
• Organic Chemistry
• Curriculum
• Analogies/Transfer
• Misconceptions/Discrepant Events
• Reactive Intermediates
• Addition Reactions
• Stereochemistry
• Epoxides

Torsional effects influence kinetic selectivity in a wide range of organic transformations. As such, textbooks commonly use Newman projections to illustrate the torsional effects that arise in their transition states. Unfortunately, these representations fall short when the reaction occurs within a ring. In many cases, the torsional preferences of the ring and the stereoelectronic (orbital) requirements of the reaction can lead to either a chair or twist-boat transition state. The aim of this communication is to shed light on these effects and to describe a new method to draw and visualize the associated chair and twist-boat transition state structures.

• 出版日期2018-7