1961
DOI: 10.1021/ja01466a040
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N-Nitrosoamides. IV. N-Nitrosoamides of Primary Carbinamines1

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Cited by 49 publications
(13 citation statements)
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“…The use of acylarylnitrosoamines as intermediates came under serious consideration. Thus Bamberger (54) and Hey et al (55) studied the use of acylarylnitrosoamines as arylating agents, while DeTar (56,57) and White (58)(59)(60) and co-workers studied the decomposition of such compounds, both in the aromatic and aliphatic series, in a variety of solvents. Finally, Denney et al (34) and Cadogan et al (35) demonstrated that the relevant aryl radical formed upon decomposition of the intermediate diazonium cation is able to abstract hydrogen atoms from the solvent to generate the desired H-substituted materials in satisfactory yields.…”
Section: +mentioning
confidence: 99%
“…The use of acylarylnitrosoamines as intermediates came under serious consideration. Thus Bamberger (54) and Hey et al (55) studied the use of acylarylnitrosoamines as arylating agents, while DeTar (56,57) and White (58)(59)(60) and co-workers studied the decomposition of such compounds, both in the aromatic and aliphatic series, in a variety of solvents. Finally, Denney et al (34) and Cadogan et al (35) demonstrated that the relevant aryl radical formed upon decomposition of the intermediate diazonium cation is able to abstract hydrogen atoms from the solvent to generate the desired H-substituted materials in satisfactory yields.…”
Section: +mentioning
confidence: 99%
“…Insightful experiments by Streitwieser & Schaeffer [9] and by White & Aufdermarch [10] support the idea that these N-nitrosoamides first go through a rate-determining cyclic substitution reaction to form transient diazoesters (21) Tables S1 and S2). Fortunately, this alkene product can be easily separated from the final alcohol product by column chromatography.…”
Section: Mechanismmentioning
confidence: 90%
“…In a series of papers which appeared in the late 50's, Huisgen et al [10] and later White [11] published results of an interesting reaction where acyl groups of N-nitroso carboxanilides were rearranged by a N-O-migration to acyloxy diazo-compounds. Although the main interest of both groups was directed towards reactions where molecular nitrogen was lost, they mentioned also a few results where the acyloxy group was simply replaced by nucleophiles.…”
Section: Introductionmentioning
confidence: 99%