Preparation of isobenzofurandiones by flash vacuum pyrolysis involving retro-Diels-Alder expulsion of ethylene and concomitant C-O cleavage of methoxy or ethylenedioxy groups

R. Slamet, Dieter Wege

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

Flash vacuum pyrolysis (fvp) of a number of substrates, prepared by hydrogenating adducts derived from dimethoxy-or ethylenedioxy-substituted benzynes and furan, affords isobenzofurandiones through retro-Diels-Alder expulsion of ethylene and C-O bond cleavage of the methoxy or ethylenedioxy groups. The parent isobenzofuran-4,5-dione is reactive and undergoes two-fold conjugate addition of water to afford 3,4-dihydroxybenzene-1,2-dicarboxaldehyde. (c) 2007 Elsevier Ltd. All rights reserved.
Original languageEnglish
Pages (from-to)12621-12628
JournalTetrahedron
Volume63
DOIs
Publication statusPublished - 2007

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