Ruthenium-catalyzed rearrangement of cis-1-ethynyl-2-vinyloxiranes to substituted phenols

Synlett

Volumn , Issue 8, 2006, Pages 1173-1176

  Maddirala, Shambabu Joseph ^a   Odedra, Arjan ^a   Taduri, Bhanu Pratap ^a   Liu, Rai Shung ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

1,2 hydrogen shift; 2,6 disubstituted phenols; cis 1 ethynyl 2 vinyloxiranes; endo dig cyclization; Ruthenium vinylidine intermediate; TpRuPPh 3(CH3CN)2PF6

Indexed keywords

1 ACYL 2 ETHYNYLCYCLOPROPANE DERIVATIVE; 1 ETHYNYL 2 VINYLOXIRANE DERIVATIVE; 1 VINYL 2 ETHYNYLCYCLOPROPANE DERIVATIVE; CARBON; CYCLOPROPANE DERIVATIVE; EPOXIDE; ETHYLENE OXIDE; ETHYLENE OXIDE DERIVATIVE; OXYGEN; PHENOL DERIVATIVE; RUTHENIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL STRUCTURE; CYCLIZATION; REACTION ANALYSIS; SUBSTITUTION REACTION;

EID: 33744485614     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-926255     Document Type: Article

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40. In a separate experiment, epoxide 12 (0.6 M) was heated alone in toluene (100 °C, 12 h), and we isolated the phenol 18 and aldehyde 21 in 4% and 10%, respectively, whereas the starting epoxide 12 was recovered in 51% (Scheme 10). (diagram presented) Scheme 10