http://www.cnr.it/ontology/cnr/individuo/prodotto/ID55071
Formylation of activated arenes by phenyl formate: implications for the mechanism of the Fries rearrangement of aryl formates (Articolo in rivista)
- Type
- Label
- Formylation of activated arenes by phenyl formate: implications for the mechanism of the Fries rearrangement of aryl formates (Articolo in rivista) (literal)
- Anno
- 2008-01-01T00:00:00+01:00 (literal)
- Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
- 10.1002/poc.1356 (literal)
- Alternative label
Bagno, A., Kantlehner, W., Saielli, G. (2008)
Formylation of activated arenes by phenyl formate: implications for the mechanism of the Fries rearrangement of aryl formates
in Journal of physical organic chemistry (Print)
(literal)
- Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
- Bagno, A., Kantlehner, W., Saielli, G. (literal)
- Pagina inizio
- Pagina fine
- Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
- Rivista
- Note
- ISI Web of Science (WOS) (literal)
- Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
- Dipartimento di Scienze Chimiche, Universita` degli Studi di Padova, Via
Marzolo, 1-35131 Padova, Italy
Institut fu¨r Organische Chemie der Universita¨t Stuttgart, Pfaffenwaldring 55,
D-70569 Stuttgart, Germany
Istituto per la Tecnologia delle Membrane del CNR, Sezione di Padova, Via
Marzolo, 1-35131 Padova, Italy (literal)
- Titolo
- Formylation of activated arenes by phenyl formate: implications for the mechanism of the Fries rearrangement of aryl formates (literal)
- Abstract
- We present an NMR and DFT investigation of the reaction of phenyl formate with 3-methoxyphenol and
3,5-dimethoxyphenol with excess BCl3. The products obtained (3-methoxy- and 3,5-dimethoxy-salicylaldehyde,
respectively) are the same as those resulting from the Fries rearrangement of 3-methoxy- and 3,5-dimethoxy-phenyl
formate. These results represent a novel regioselective synthetic route to aromatic aldehydes, using phenyl formate
as a source of formylating agent. They also unambiguously prove that the Fries rearrangement of aryl formates
(that we recently investigated in J. Org. Chem. 71, 9331-9340, 2006) is intermolecular: the intermediate formyl
chloride is released in situ and, in turn, it formylates the intermediate dichloroborate ester of 3-methoxy- and
3,5-dimethoxy-phenol in a second independent step. The --BCl2 moiety bound to the aryl oxygen of the substituted
phenol interacts with the formyl chloride strongly favouring the ortho substitution. (literal)
- Prodotto di
- Autore CNR
Incoming links:
- Prodotto
- Autore CNR di
- Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#rivistaDi