Welcome to LookChem.com Sign In|Join Free

Article Doi

Synthesis of Substituted Aromatic Compounds by Diels-Alder Reactions of Alkoxycyclobutenes Produced via Photocycloadditions between Vinyl Ethers and 1,3-Dione Enol Esters

DOI: 10.1039/P19830001919

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 1919 - 1923 (1983)

Update date:2022-08-03

Topics:

Authors:

Barker, Andrew J.Barker, Andrew J.

Begley, Michael J.Begley, Michael J.

Birch, Alan M.Birch, Alan M.

Pattenden, GeraldPattenden, Gerald

Read Full Text PDF DownLoad Join now for total 90,000,000 free articles

Article abstract of DOI:10.1039/P19830001919

The adducts (5) obtained from <2 + 2> photocycloaddition of ethyl vinyl ether to the 1,3-dione enol acetate (4) rapidly loses acetic acid producing the ethoxycyclobutene (7).On being warmed in the presence of a dienophile, the ethoxycyclobutene (7) undergoes electrocyclic ring-opening to give the ethoxydienone (8) followed by <4 + 2> cycloaddition to produce Diels-Alder adducts ; elimination of ethanol from (10) gives the dimethyl phthalate (11).In a 'one-pot' reaction, heating a solution of (5) with 1,4-naphthoquinone in xylene containing aluminia leads to the substituted anthraquinone (12) in 95percent yield.On storage at 0 deg C for a few days the ethoxycyclobutene (7) is converted into the crystalline dimer (9) via the transient ethoxydienone (8); the structure of (9) followed from X-ray measurements.An analogous dimer (14) was produced during attempts to effect an intramolecular Diels-Alder reaction from the bicyclic ether (13).

View More

Products guided by the article

Product name:6-acetoxy-7-ethoxy-4,4-dimethylbicyclo<4.2.0>octan-2-one

Cas No:88082-89-7

88082-89-7

R&D Labs maybe for 88082-89-7

Relevant to this article

Hot Product