Diels-Alder Cycloaddition of Tetraphenylcyclopentadienone and 1,3,5-Hexatriynes

Sale AC, Murray AH, Prenzel D, Hampel F, De Luca L, Tykwinski R (2016)

Publication Type: Journal article

Publication year: 2016

Journal

Book Volume: 2016

Pages Range: 2274-2283

Journal Issue: 13

DOI: 10.1002/ejoc.201600116

Abstract

Diels--Alder cycloaddition reactions of 1,3,5-hexatriynes with tetraphenylcyclopentadienone have been performed, and mainly gave 1,2-diethynyl-3,4,5,6-tetraphenylbenzene derivatives as products. The Diels--Alder reactions were optimized under conventional heating and microwave irradiation conditions, and showed good selectivity towards the central carbon--carbon triple bond of the triyne. Empirical evidence suggests that the selectivity of the reaction is governed predominantly by the steric demands of the end-groups of the triyne. Several of the Diels--Alder products could be further elaborated by a sequence of desilylation and oxidative homocoupling to provide dimeric products. The homocoupling reaction was optimized by Pd catalysis. The X-ray crystallographic analysis of two derivatives is reported.

Authors with CRIS profile

Additional Organisation(s)

Involved external institutions

Università degli Studi di Sassari (UNISS) Italy (IT)

How to cite

APA:

Sale, A.C., Murray, A.H., Prenzel, D., Hampel, F., De Luca, L., & Tykwinski, R. (2016). Diels-Alder Cycloaddition of Tetraphenylcyclopentadienone and 1,3,5-Hexatriynes. European Journal of Organic Chemistry, 2016(13), 2274-2283. https://dx.doi.org/10.1002/ejoc.201600116

MLA:

Sale, Anna Chiara, et al. "Diels-Alder Cycloaddition of Tetraphenylcyclopentadienone and 1,3,5-Hexatriynes." European Journal of Organic Chemistry 2016.13 (2016): 2274-2283.

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