71473-94-4Relevant articles and documents
Azirine/oxindole ring enlargement via amidinium intermediates
Mekhael, Maged K. G.,Bienz, Stefan,Linden, Anthony,Heimgartner, Heinz
, p. 2385 - 2404 (2007/10/03)
A novel general method for the synthesis of oxindoles, namely the 'azirine/oxindole ring enlargement via amidinium-intermediates' has been established: the reaction of 2H-azirin-3-amines 1 with BF3· OEt2 in THF solution at -78° leads
Amine-Induced Reactions of Diacyl Peroxides
Srinivas, Shamala,Taylor, K. Grant
, p. 1779 - 1786 (2007/10/02)
The decompositions of 3-chlorobenzoyl cyclobutylformyl peroxide (3a), and 3-chlorobenzoyl cyclopropylacetyl peroxide (3b) induced by 1-azabicyclooctane (Q), N1,N1,N4,N4-tetramethyl-1,4-benzenediamine (W), 1,4-diazabicyclooctane (DABCO), and N,N-dimethylaniline (DMA) were investigated.Peroxides 3 were selected for study because distinctive product patterns were expected from decompositions induced by the alternative SN2 and SET pathways.Q and W were selected as amines likely to react by the SN2 and SET pathways, respectively.Q reacted with3 to give products characteristic of the intermediacy of an ion pair (general structure: R3NOCOC4H7+ArCO2-) formed by the SN2 pathway, while W reacted with 3 to give rapid formation of the C4H7CO2 radical, indicative of an SET pathway.Based on the results with Q and W, we interpret the results with DABCO and DMA to indicate that both induce the decomposition of 3 by the SN2 pathway.Thus, peroxides 3 have been shown to be structurally sensitive to the modes of their induced decomposition, and are, potentially, mechanistic probes for ascertaining the mechanism of induced peroxide decomposition by closed-shell molecules.
