Premium
Diels–Alder Cycloaddition of Tetraphenylcyclopentadienone and 1,3,5‐Hexatriynes
Author(s) -
Sale Anna Chiara,
Murray Adrian H.,
Prenzel Dominik,
Hampel Frank,
De Luca Lidia,
Tykwinski Rik R.
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600116
Subject(s) - cycloaddition , chemistry , steric effects , selectivity , diels–alder reaction , catalysis , microwave irradiation , triple bond , medicinal chemistry , organic chemistry , stereochemistry , double bond
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.