100532-35-2Relevant academic research and scientific papers
Ruthenium-catalyzed rearrangement of cis-1-ethynyl-2-vinyloxiranes to substituted phenols
Maddirala, Shambabu Joseph,Odedra, Arjan,Taduri, Bhanu Pratap,Liu, Rai-Shung
, p. 1173 - 1176 (2007/10/03)
Catalytic cyclization of cis-1-ethynyl-2-vinyloxiranes was implemented with TpRuPPh3(CH3CN)2PF6 catalyst (10 mol%), to give 2,6-disubstituted phenols in reasonable yields. Under similar conditions, 1,1,2,2-tetrasubstituted oxirane gave the 2,3,6-trisubstituted phenol with skeleton reorganization. On the basis of 2H- and l3C-labeling results, we propose that the reaction mechanism involves electrocyclization of ruthenium-vinylidene intermediate with cleavage of the carbon-oxygen bond of the epoxide. Georg Thieme Verlag Stuttgart.
