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• W2142175154 abstract "Cyclopropanediamines, 4. – Synthesis and 1H-NMR Spectra of Pure Diastereomers of 1,2-Cyclopropanediamines and 1,2-Cyclopropanediammonium Dibromides The efficient preparation of pure diastereomers of N,N′-(1,2-cyclopropanediyl)diurethanes 16–18 and -diammonium dibromides 4, 19, and 20 is reported. Curtius rearrangement of cis- and trans-1,2-cyclopropandicarboxylic dihydrazides 14 yields di(O-benzyl) diurethanes 16 on a 10-100 g scale. The cis-1,2-cyclopropanedicarboxylic dihydrazides cis-14 tend to form bicyclic products. Thus, from cis-14a a small amount of 22a is obtained besides the diurethane cis-16a. Cyclisation is the main reaction in the case of cis-1,2-dimethyl-1,2-cyclopropanedicarboxylic hydrazide (cis-14e) which affords the bicyclic products 22e and 24, but no diurethane. The 1,2-dimethyl-1,2-cyclopropanedicarboxylic acid (27) reacts with diphenyl phosphorazidate to produce the monobenzyl ester 29. The diurethanes 16 are methylated (→ 17) and benzylated (→ 18) at both nitrogen atoms. The benzyloxycarbonyl group is removed from the diurethanes 16–18 by the action of hydrogen bromide in acetic acid to yield the 1,2-cyclopropanediammonium dibromides 4, 19, and 20. The 1H-NMR spectra are analysed and the results are employed as criteria for the configurations." @default.
• W2142175154 created "2016-06-24" @default.
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• W2142175154 date "1994-06-13" @default.
• W2142175154 modified "2023-10-16" @default.
• W2142175154 title "Cyclopropandiamine, 4. Synthese und1H-NMR-Spektren diastereomerenreiner 1,2-Cyclopropandiamine und 1,2-Cyclopropandiammonium-dibromide" @default.
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• W2142175154 doi "https://doi.org/10.1002/jlac.199419940607" @default.
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