Related Experiment Video
Updated: Aug 26, 2026

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Synthesis and intramolecular reactions of trans-cyclohexyl-1,2-bisacrylate
John R Williams1, Jianbin Ma, Peter Wepplo
1Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122-2585, USA. john.r.williams@temple.edu
Abstract:
Photocycloaddition of dimethyl cyclobut-1-ene-1,2-dicarboxylate (1) with cyclohexene (7) afforded two photoadducts 8 and 9 in 44% and 28% yields, respectively. Spontaneous thermal isomerization of 8 gave (4Z,10Z)-dimethyl cyclodeca-4,10-diene-1,4-dicarboxylate (10), which subsequently isomerized to produce trans-1,2-cyclohexanebis-alpha-acrylic acid dimethyl ester 11. Hydride reduction of the bisacrylate 11 gave the trans-octahydro-1H-inden-2-ols 12a and 15 via a novel, stereoselective, intramolecular reaction. Reaction of the bisacrylate 11 with methyllithium afforded the bis-tertiary alcohol 16. In contrast, lithium dimethylcuprate reacted with the bisacrylate 11 to give the trans-hexahydro-1H-inden-2-one 17 in high yield via a novel, stereoselective, intramolecular reaction.
Related Concept Videos
Cycloaddition Reactions: Overview
Disubstituted Cyclohexanes: cis-trans Isomerism
In cyclohexane, the substituents can occupy different positions generating distinct isomers.
Thermal and Photochemical Electrocyclic Reactions: Overview
Cycloaddition Reactions: MO Requirements for Thermal Activation
Aromatic Hydrocarbon Cations: Structural Overview
Removing one hydrogen from the intervening CH2 group with both...
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

