Reinvestigation relative to the regioselectivity of the aryne cycloaddition. Synthesis of the tricyclo[6.2.0.0 2,5]-1,5,7-triene-3,10-dione

A rapid and total synthesis of a tricyclo[6.2.0.0]deca-1,5,7-triene-3,10-dione 7b is described. Its synthesis involves the [2+2] cycloaddition of a benzyne to 2-methylene-1,3-dioxepane followed by hydrolysis to the corresponding ketone. This reaction is totally regioselective and the real structure...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron letters 2001-11, Vol.42 (46), p.8147-8149
Main Authors: Maurin, Philippe, Ibrahim-Ouali, Malika, Santelli, Maurice
Format: Article
Language:English
Subjects:
2-methylene-1,3-dioxepane
[2+2] cycloaddition
benzocyclobutene
benzyne
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A rapid and total synthesis of a tricyclo[6.2.0.0]deca-1,5,7-triene-3,10-dione 7b is described. Its synthesis involves the [2+2] cycloaddition of a benzyne to 2-methylene-1,3-dioxepane followed by hydrolysis to the corresponding ketone. This reaction is totally regioselective and the real structure of the molecule is given thanks notably to the X-ray crystal structure of the intermediate benzo-bis-cyclobutene. A novel ‘benzo-bis-cyclobutenone’ is synthesized by a two-step procedure involving a [2+2] cycloaddition of a benzyne to 2-methylene-1,3-dioxepane followed by hydrolysis.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(01)01727-0