Synthesis of Chromanes and 4H-Chromenes: Exploring the Oxidation of 2H-Chromenes and Dihydro-1-benzoxepines by Hypervalent Iodine(III)


Autoria(s): Ahmad, Anees; Silva, Luiz F., Jr.
Contribuinte(s)

UNIVERSIDADE DE SÃO PAULO

Data(s)

04/11/2013

04/11/2013

2012

Resumo

The reaction of various oxygen-containing benzo-fused cycloalkenes were studied with the hypervalent iodine reagent hydroxy(tosyloxy) iodo]benzene [PhI(OH)OTs, HTIB]. 2H-Chromene and 4-methyl-2H-chromene resulted in substituted 4H-chromene and cis-3,4-dialkoxy-4-methyl-3,4-dihydro-2H-chromenes, respectively. Ring contraction to chromanes and benzofurans was observed for dihydrobenzoxepines and 2,2-dimethyl-2H-chromenes, respectively.

CAPES

Capes

Fapesp

FAPESP

CNPq

CNPQ

Identificador

SYNTHESIS-STUTTGART, STUTTGART, v. 44, n. 23, supl. 1, Part 6, pp. 3671-3677, DEC, 2012

0039-7881

http://www.producao.usp.br/handle/BDPI/37838

10.1055/s-0032-1317497

http://dx.doi.org/10.1055/s-0032-1317497

Idioma(s)

eng

Publicador

GEORG THIEME VERLAG KG

STUTTGART

Relação

SYNTHESIS-STUTTGART

Direitos

closedAccess

Copyright GEORG THIEME VERLAG KG

Palavras-Chave #CHROMENES #CHROMANES #KOSER'S REAGENT #RING CONTRACTION #HYPERVALENT IODINE #RING CONTRACTION #ALPHA-TOSYLOXYLATION #KETONES #<HYDROXY(TOSYLOXY)IODO>BENZENE #1,2-DIHYDRONAPHTHALENES #DISCOVERY #ORGANOIODINE #INHIBITORS #AMINATION #EXPANSION #CHEMISTRY, ORGANIC
Tipo

article

original article

publishedVersion