The exploration of different reaction conditions aiming to obtain both 2,3-dihydro-1,4-benzoxathiine-2-yl derivatives and 2,3-dihydro-1,4-benzoxathiine-3-yl ones is reported. The treatment of 1,2-mercaptophenol with an organic base and a specific 2-bromo acrylate results in a solvent- and substrate-dependent exclusive solvation of O- and S-anions, thus managing the regioselectivity.
How reaction conditions may influence the regioselectivity in the synthesis of 2,3-dihydro-1,4-benzoxathiine derivatives / A. Casiraghi, E. Valoti, L. Suigo, A. Artasensi, E. Sorvillo, V. Straniero. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 83:21(2018), pp. 13217-13227.
How reaction conditions may influence the regioselectivity in the synthesis of 2,3-dihydro-1,4-benzoxathiine derivatives
A. Casiraghi;E. Valoti;L. Suigo;A. Artasensi;V. Straniero
2018
Abstract
The exploration of different reaction conditions aiming to obtain both 2,3-dihydro-1,4-benzoxathiine-2-yl derivatives and 2,3-dihydro-1,4-benzoxathiine-3-yl ones is reported. The treatment of 1,2-mercaptophenol with an organic base and a specific 2-bromo acrylate results in a solvent- and substrate-dependent exclusive solvation of O- and S-anions, thus managing the regioselectivity.
| File | Dimensione | Formato | |
|---|---|---|---|
|
Straniero_JOC2018_FinalRevision.pdf
accesso aperto
Descrizione: Versione post-print
Tipologia:
Post-print, accepted manuscript ecc. (versione accettata dall'editore)
Dimensione
911.58 kB
Formato
Adobe PDF
|
911.58 kB | Adobe PDF | Visualizza/Apri |
|
acs.joc.8b02012.pdf
accesso riservato
Tipologia:
Publisher's version/PDF
Dimensione
3.12 MB
Formato
Adobe PDF
|
3.12 MB | Adobe PDF | Visualizza/Apri Richiedi una copia |
Pubblicazioni consigliate
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
