Journal article

Publication year: 2005

Pages: 1881-1884

Journal: The Journal of Organic Chemistry

Volume number: 70

Issue number: 5

ISSN: 0022-3263

DOI Link: https://doi.org/10.1021/jo0485132

Publisher: American Chemical Society

Abstract: 
[GRAPHICS]Photochemical cyclization of compound 1, a homoenediyne (-CCC=CCH2CC-) bearing two ethynylanthracene chromophores, yields two isomeric dihydrocyclopent[alpha]indene ring systems, spiro-fused to the 9-position of a 9,10-dihydroanthracene moiety. Evidence of a photochemically initiated diradical cyclization pathway is proposed on the basis of (i) hydrogen abstraction from reaction with 1,4-cyclohexadiene (1,4-CHD) and (ii) the observation of 1,4-addition of benzene (solvent). The reaction was further analyzed by a complete density functional theory (DFT) study, using an unrestricted approach (UBLYP) with a 6-31G* basis set for the open-shell triplet states of the reactants, products, and diradical intermediates to model the photochemical nature of observed transformation. A mechanism detailing the observed cyclization/addition reaction is proposed.

Harvard Citation style: Marsella, M., Yoon, K., Estassi, S., Tham, F., Borchardt, D., Bui, B., et al. (2005) 1,4-addition of benzene to a dihydrocyclopent[a]indene diradical: Synthesis and DFT study, The Journal of Organic Chemistry, 70(5), pp. 1881-1884. https://doi.org/10.1021/jo0485132

APA Citation style: Marsella, M., Yoon, K., Estassi, S., Tham, F., Borchardt, D., Bui, B., & Schreiner, P. (2005). 1,4-addition of benzene to a dihydrocyclopent[a]indene diradical: Synthesis and DFT study. The Journal of Organic Chemistry. 70(5), 1881-1884. https://doi.org/10.1021/jo0485132