Diaziridines. II. The Addition of Diaziridines to Electrophilic Acetylenes

Harold W. Heine, Thomas It Hoye, Paul G. Williard, Rebecca Cowan Hoye

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

Addition of 3,3-dialkyl-, 1,3-dialkyl-, and 1,3,3-trialkyldiaziridines to dibenzoylacetylene, diethyl acetylenedi-oarboxylate, and ethyl propiolate gives, generally, adducts in which the diaziridine ring is no longer intact. For example, addition of 1,3-dialkyl- and 1,3,3-trialkyldiaziridines to dibenzoylacetylene forms 2-(alkylidenehydrazino)-l,4-diphenyl-2-butene-l,4-diones (2). Evidence is presented that it is the alkylated nitrogen of 1-methyl-3,3-pentamethylenediaziridine which adds to the triple bond of dibenzoylacetylene. Stereochemical studies show that diaziridines add to ethyl propiolate to give trans adducts. Hydrolysis of 2-(alkylidenehydrazino)-l,4-diphenyl-2-butene-l,4-diones is shown to be a useful method for the preparation of l-alkyl-3-phenyl-5-benzoylpyrazoles.

Original languageEnglish (US)
Pages (from-to)2984-2988
Number of pages5
JournalJournal of Organic Chemistry
Volume38
Issue number17
DOIs
StatePublished - Aug 1 1973

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Alkynes
Hydrolysis
Nitrogen
2-butene
ethyl propiolate
diphenyl

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Diaziridines. II. The Addition of Diaziridines to Electrophilic Acetylenes. / Heine, Harold W.; Hoye, Thomas It; Williard, Paul G.; Hoye, Rebecca Cowan.

In: Journal of Organic Chemistry, Vol. 38, No. 17, 01.08.1973, p. 2984-2988.

Research output: Contribution to journalArticle

Heine, Harold W. ; Hoye, Thomas It ; Williard, Paul G. ; Hoye, Rebecca Cowan. / Diaziridines. II. The Addition of Diaziridines to Electrophilic Acetylenes. In: Journal of Organic Chemistry. 1973 ; Vol. 38, No. 17. pp. 2984-2988.
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