1450894-32-2Relevant academic research and scientific papers
Arynes double bond insertion/nucleophilic addition with vinylogous amides and carbodiimides
Wu, Chao,Li, Ran,Tang, Huarong,Fu, Haixing,Ren, Hailong,Wang, Xuemei,Wu, Chunrui,Shi, Feng
, p. 1344 - 1355 (2014/03/21)
Arynes are shown to insert into some C=X double bonds, leading to benzannulated four-membered rings. The strain of these rings allow for a ready, spontaneous opening to afford o-quinomethide analogues. Subsequent nucleophilic addition re-aromatizes the intermediates to achieve ortho-difunctionalization of arynes. In this report, we describe the aryne insertion into the C=C double bonds of vinylogous amides and the C=N double bonds of carbodiimides. The correlation and comparison with aryne single bond insertion chemistry will be discussed. Computational studies for the ring-opening step, as well as the nature of the o-quinomethide intermediates, will also be discussed.
Reaction of arynes with vinylogous amides: Nucleophilic addition to the ortho-quinodimethide intermediate
Li, Ran,Wang, Xuemei,Wei, Zhibin,Wu, Chunrui,Shi, Feng
supporting information, p. 4366 - 4369 (2013/09/24)
The reaction of arynes with vinylogous amides containing no free N-H bonds proceeds in a [2 + 2] cycloaddition fashion at ambient temperature. The electronic properties of the vinylogous amides allow for the cycloadducts undergoing a facile ring-opening p
