82669-94-1Relevant articles and documents
Unlocking the 5-exo Pathway with the AuI-Catalyzed Alkoxycyclization of 1,3-Dien-5-ynes
Virumbrales, Cintia,Suárez-Pantiga, Samuel,Marín-Luna, Marta,Silva López, Carlos,Sanz, Roberto
, p. 8443 - 8451 (2020)
The first general regio- and stereoselective 5-exo gold(I)-catalyzed alkoxycyclization of a specific class of 1,5-enynes such as 1,3-dien-5-ynes has been described, despite 1,5-enynes being known to almost invariably proceed via endo cyclizations under gold-catalysis. The configuration of the terminal alkene in the starting 1,3-dien-5-yne plays a crucial role on the regiochemical outcome of the reaction. A wide variety of interesting alkoxy-functionalized alkylidenecyclopentenes have been synthesized from 1-monosubstituted (E)-1,3-dien-5-ynes. On the contrary, the corresponding Z isomers evolve affording formal 6-endo cyclization products. In addition, mechanistic exploration supports a highly stabilized carbocation as a key intermediate instead of a highly constrained cyclopropyl gold carbene from E isomers, and also accounts for the well differentiated reactivity observed between both E/Z geometrical isomers as well as for the stereochemical outcome of the reaction.
Etude de la reactivite du methyl-2 tetrahydro-5,6,7,8 naphtalene vis-a-vis des reactifs electrophiles et du radical libre phenyle
Bongue-Boma, Raymonde,Rinaudo, Jean,Bonnier, Jane-Marie
, p. 52 - 58 (2007/10/02)
The reactivity of 2-methyl-5,6,7,8-tetrahydronaphthalene towards electrophilic reagents (CH3CO(1+), C6H5CO(1+), NO2(1+), Br(1+) and Ph(1+)) and the phenyl free radical is described.For Friedel-Crafts acetylation and bromination the reaction shows a high i
