TY - JOUR
T1 - Diaziridines. II. The Addition of Diaziridines to Electrophilic Acetylenes
AU - Heine, Harold W.
AU - Hoye, Thomas It
AU - Williard, Paul G.
AU - Hoye, Rebecca Cowan
PY - 1973/8/1
Y1 - 1973/8/1
N2 - 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.
AB - 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.
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U2 - 10.1021/jo00957a014
DO - 10.1021/jo00957a014
M3 - Article
AN - SCOPUS:0042418578
SN - 0022-3263
VL - 38
SP - 2984
EP - 2988
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 17
ER -