The 4,4'-(1,2-ethanediyl)bisbenzyl biradical: its generation, detection, and (photo)chemical behavior in solution

M A Miranda; E Font-Sanchis; J Pérez-Prieto; J C Scaiano

doi:10.1021/jo001623y

The 4,4'-(1,2-ethanediyl)bisbenzyl biradical: its generation, detection, and (photo)chemical behavior in solution

J Org Chem. 2001 Apr 20;66(8):2717-21. doi: 10.1021/jo001623y.

Authors

M A Miranda¹, E Font-Sanchis, J Pérez-Prieto, J C Scaiano

Affiliation

¹ Instituto de Tecnología Química UPV-CSIC/Departamento de Química, Universidad Politécnica de Valencia, Camino de Vera s/n, Valencia, 46071 Spain.

PMID: 11304192
DOI: 10.1021/jo001623y

Abstract

The 4,4'-(1,2-ethanediyl)bisbenzyl biradical (2) is clearly and efficiently generated by photolysis of [3.2]paracyclophane-2-one (8) in cyclohexane solution. This intermediate is also formed via two-photon processes from [2.2]paracyclophane (3) and 1,2-bis(4-chloromethylphenyl)ethane (4). The products arising thermally from biradical 2 are [2.2]paracyclophane and [2.2.2.2]paracyclophane (11) (under high-intensity conditions). Furthermore, two-laser two-color flash photolysis shows that biradical 2 is photostable in solution at room temperature. Thus, formation of p-xylylene (1) from 2 occurs neither thermally nor photochemically.