Diazo group transfer reactions are transformations in which an intact diazo unit is transferred from a donor to an acceptor molecule <67AG786, 67AG(E)733, 72S351>. This is undoubtedly the most versatile class of reactions for the synthesis of a-diazo carbonyl and a-diazo ß-dicarbonyl compounds.The most useful substrates for diazo group transfer are those possessing active methylene groups. For example, diazo transfer to ß-dicarbonyl compounds from sulfonyl azides is performed in the presence of tertiary amine bases . Because of the mildness, simplicity and reliability of this reaction, it has replaced amine diazotization as the method of choice for the preparation of a-diazo ß-dicarbonyl compounds. In most cases, diazo group transfer to an active methylene compound proceeds via an intermediate triazine which is formed by attack on the azide by the anion of the active methylene compound. Spontaneous decomposition of this intermediate, accompanied by a proton shift, then leads to the product diazo compound. A wide variety of azides, including tosyl azide <67AG786, 67AG(E)733, 90CC652>, methanesulfonyl azide <86JOC4077>, p-carboxybenzenesulfonyl azide <68JOC3610> and azidotris(diethylamino)phosphonium bromide <90TL4987>, have been used as diazo transfer reagents in this reaction.
diazo ketones, alkanes, synthesis, compounds, transformations
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