10043-37-5Relevant articles and documents
Solvent-dependent competitive rearrangements of cyclic tertiary propargylamine N-oxides
Szabo, Anna,Galstnibos-Farago, Agnes,Mucsi, Zoltan,Timari, Geza,Vasvari-Debreczy, Lelle,Hermecz, Istvan
, p. 687 - 694 (2007/10/03)
In protic media, cyclic propargylamine N-oxides 1 undergo solvent-dependent competitive rearrangements leading to enamino aldehydes 5, acrylamides 3, and secondary amines 4. The ratios of the products are evaluated and the possible mechanism of the compet
Reaction of Cyclopropanamines with Hypochlorite
Vaidyanathan, Ganesan,Wilson, Joseph W.
, p. 1815 - 1820 (2007/10/02)
Ethylene was formed in 65percent yield when 1-(1-piperidino)cyclopropanol 6, was treated with hypochlorite.This observation raised the possibility that 1-aminocyclopropanecarboxylic acids (ACCs) could yield ethylene by a mechanism that involves (1) decarboxylation to a 1-aminocyclopropanol, followed by (2) a fragmentation of the carbinolamine to ethylene induced by a hypochlorite equivalent.Although this mechanism could be ruled out only for 1e, no evidence could be found for it in the reactions of other ACCs, 1a-f, with hypochlorite.The fact that 1b-cis-2,3-d2 yieldedonly ethylene-cis-1,2-d2 is consistent with either the mechanism described above or a nitrenium ion mechanism.In the reaction of cyclopropanamines with neutral hypochlorite, ethylene is not the major product.From the primary and secondary amino acids 1a-c, a 3-hydroxypropanenitrile or propanamide, 2a-c, probably the product of a nucleophilic ring-opening step followed by decarboxylation, is formed.Similar products are formed from other cyclopropanamines: 2a from 1g, 2d from 1h, 2e and 2f from 1i, and lactone 5 from 1j.