Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact: purchase@heterocycles.com

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

Report | Regular issue | Vol 14, No. 1, 1980, pp.51-54
Published online, 1st January, 1970
DOI: 10.3987/R-1980-01-0051
Benzodioxole Chemistry. 4. Concerning the Aromatization of Carbonyl-bridged Cyclic Carbonates Effected by Potassium Carbonate in Aqueous Dimethylformamide

Ernest A. Harrison, Jr.*

*Department of Chemistry, The Pennsylvania State University, York Campus, P1031 Edgecomb Avenue, York, Pennsylvania 17403, U.S.A.

Abstract

Three 4,5,6,7-tetrasubstituted 3a,4,7,7a-Tetrahydro-4,7-methano-1,3,-benzodioxole-2,8-diones (1a-c) containing electron-withdrawing groups in the 4- and 7-positions undergo clean, high-yield conversion to aromatic products 6a-c in 4% aqueous dimethylformamide containing no added potassium carbonate. By comparison, one benzodioxoledione (1d) containing electron-donating groups in the same positions yields no aromatic product under these conditions. By allowing the reaction of 1b with DMF/H2O to proceed for only 24 h good yields of hydroxyacid 4b (36%) and hydrocarbon 6b (40%) are obtained. Taken in conjunction with the substituent-dependent reactivity, isolation of 4b lends strong support to a previous mechanistic proposal; while discovery of the fact that the aromatization reaction can proceed without added base broadens the scope of its synthetic potential.