Journal article

Authors list: Rickhaus, M; Belanger, AP; Wegner, HA; Scott, LT

Publication year: 2010

Pages: 7358-7364

Journal: The Journal of Organic Chemistry

Volume number: 75

Issue number: 21

ISSN: 0022-3263

DOI Link: https://doi.org/10.1021/jo101635z

Publisher: American Chemical Society

Abstract: 
Oxidative cyclization of 1, 1 '-binaphthyl (1) to perylene (2) can be achieved in essentially quantitative yield by the action of three or more equivalents of potassium metal in hot tetrahydrofuran. An overall reaction mechanism is proposed that accounts for all of the experimental observations reported by previous investigators and those from the present studies. The trans-6a,6b-dihydroperylene dianion (6(2-)) is believed lobe the pivotal intermediate from which H(2), is lost. A radical chain reaction involving free hydrogen atoms (H(center dot)) in the two-step propagation cycle is proposed to explain the formation of H(2) from 6(2-). Anionic cyclodehydrogenations of this sort are complementary to those performed under strongly acidic/oxidizing conditions, photochemically, or thermally (flash vacuum pyrolysis), and a better understanding of how they occur, together with the optimized synthetic protocol reported here, should encourage their wider use in organic synthesis.

Harvard Citation style: Rickhaus, M., Belanger, A., Wegner, H. and Scott, L. (2010) An Oxidation Induced by Potassium Metal. Studies on the Anionic Cyclodehydrogenation of 1,1 '-Binaphthyl to Perylene, The Journal of Organic Chemistry, 75(21), pp. 7358-7364. https://doi.org/10.1021/jo101635z

APA Citation style: Rickhaus, M., Belanger, A., Wegner, H., & Scott, L. (2010). An Oxidation Induced by Potassium Metal. Studies on the Anionic Cyclodehydrogenation of 1,1 '-Binaphthyl to Perylene. The Journal of Organic Chemistry. 75(21), 7358-7364. https://doi.org/10.1021/jo101635z