Abstract
The synthesis of (RS)-2- or (RS)-3-methoxy-2,3-dihydro-5H-1,4-benzodioxepins and (RS)-5- or (RS)-3-methoxy-2,3,5,6-tetrahydro-8H-benzo-[1,4,7]-trioxecins has been developed. The mechanism of such a reaction via the boron trifluoride etherate-promoted transformation of 2-(methoxyethoxymethoxy)benzyloxyacetaldehyde dimethyl acetals or 2-(methoxyethoxymethoxymethyl)phenyloxyacetaldehyde dimethyl acetals has been proposed. Transannular versions of the reaction results in the facile ring contraction of 12-membered intermediates to the 10- and to 7-membered benzene-fused O,O-acetals. The characterization of the by-products strongly supports the mechanisms proposed.
Lingua originale | English |
---|---|
pagine (da-a) | 11453-11464 |
Numero di pagine | 12 |
Rivista | Tetrahedron |
Volume | 60 |
Stato di pubblicazione | Published - 2004 |
All Science Journal Classification (ASJC) codes
- ???subjectarea.asjc.1300.1303???
- ???subjectarea.asjc.3000.3002???
- ???subjectarea.asjc.1600.1605???