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A dehydrogenated cycloadduct of N-phenylmaleimide and the azomethine ylide derived from ninhydrine and phenylalanine: Structure and conformation

TitleA dehydrogenated cycloadduct of N-phenylmaleimide and the azomethine ylide derived from ninhydrine and phenylalanine: Structure and conformation
Publication TypeJournal Article
Year of Publication2001
AuthorsPreu, L, Kliegel, W, Rettig, SJ, Trotter, J
JournalMonatshefte Fur Chemie
Volume132
Pagination1213-1224
Date PublishedOct
Type of ArticleArticle
ISBN Number0026-9247
Keywordsdynamic H-1 NMR spectroscopy, molecular modeling, spiro compounds, X-ray structure determination
Abstract

{The structure of the dehydrogenation product 1 ’ ,3a ’ -dihydro-3 ’-((1,3-dioxoindan-2-ylidene)-phenyl-methyl)-5 ’ -phenyl-spiro-(indan-2,1 ’ -pyrrolo[3,4-c]pyrrole)-1,3,4 ’ ,6 ’-(5 ’H, 6a ’H)-tetrone derived from the cycloadducts (+/-)-(3a ’S,6a ’R)-1 ’ ,3a ’ -dihydro-3 ’-((R)-alpha-(1,3-dioxoindanyl)-benzyl)-5 ’ -phenyl-spiro-(indan-2,1 ’ -pyrrolo[3,4-c]pyrrole)-1,3,4 ’ ,6 ’ (5H,6a ’H)-tetrone and/or (+/-)-(3a ’S,6a ’R)-1 ’ ,3a ’ -dihydro-3 ’-((S)-alpha-(1,3-dioxoindanyl)-benzyl)-5 ’ -phenyl-spiro-(indan-2,1 ’ -pyrrolo[3,4-c]pyrrole)-1,3,4 ’ ,6 ’ (5H,6a ’H)-tetrone, which were synthesized by 1,3-dipolar cycloaddition of N-phenylmaleimide to 2-((2-(1,3-dioxoindan-2-yl)-2-phenyl-ethenyl)-imino)-indan-1,3-dione, was determined by X-ray analysis. Crystal data (CCD, 180K): rhombohedral, R (3) over bar

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