Controlling factors determining the regiochemistry of intramolecular alkoxymercuration
The intramolecular alkoxymercuration of (E)-5-arylpent-4-en-1-ols indicated that the regioselectivity is closely related to the Hammett constants of the para-substituents on the benzene ring. Large solvent effects on the regioselectivity were also observe
Aryl Boronic Acid Catalysed Dehydrative Substitution of Benzylic Alcohols for C?O Bond Formation
A combination of pentafluorophenylboronic acid and oxalic acid catalyses the dehydrative substitution of benzylic alcohols with a second alcohol to form new C?O bonds. This method has been applied to the intermolecular substitution of benzylic alcohols to form symmetrical ethers, intramolecular cyclisations of diols to form aryl-substituted tetrahydrofuran and tetrahydropyran derivatives, and intermolecular crossed-etherification reactions between two different alcohols. Mechanistic control experiments have identified a potential catalytic intermediate formed between the aryl boronic acid and oxalic acid.
Estopi?á-Durán, Susana,Donnelly, Liam J.,Mclean, Euan B.,Hockin, Bryony M.,Slawin, Alexandra M. Z.,Taylor, James E.
p. 3950 - 3956
(2019/02/16)
Polar and steric substituent effects in 5-exo-trig cyclizations of 1-aryl-4-penten-1-oxyl radicals
A series of 1-aryl-substituted 4-penten-1-oxyl radicals 2 were generated from parent N-alkoxypyridinethiones 6. The intermediates 2 undergo 5-exo-trig cyclizations which are sensitive to polar and steric substituent effects. Thus, para groups in the aroma
Hartung, Jens,Hiller, Margit,Schmidt, Philipp
p. 1425 - 1436
(2007/10/03)
SUBSTITUTION REACTIONS OF 2-BENZENESULPHONYL CYCLIC ETHERS WITH CARBON NUCLEOPHILES
Direct substitution of 2-benzenesulphonylcyclic ethers was studied using a variety of carbon nucleophiles.These nucleophiles included organozinc reagents (derived from aryl, vinyl and alkynyl Grignard reagents) or silyl enol ethers, silyl ketene acetals,
Brown, Dearg S.,Bruno, Maurizio,Davenport, Raymond J.,Ley, Steven V.
p. 4293 - 4308
(2007/10/02)
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