3422-06-8Relevant academic research and scientific papers
An efficient one-pot synthesis of azidoformates from alcohols using triphosgene: Synthesis of N-carbobenzyloxy azetidin-2-ones
Patil,Parveen, Ghazala,Gumaste,Bhawal,Deshmukh
, p. 1455 - 1458 (2007/10/03)
An efficient use of triphosgene for the preparation of various azidoformates from alcohols and sodium azide is described. The method is applied to various chiral alcohols including glucose diacetonide to get the corresponding azidoformates. One of these azidoformates has been successfully utilized for the synthesis of N-carbobenzyloxy-β-lactams.
Alkoxycarbonylnitrenes as Selective Intramolecular CH-Insertion Reagents in Alicyclic Chemistry
Marais, Pierre C.,Meth-Cohn, Otto
, p. 1553 - 1561 (2007/10/02)
Intramolecular CH-insertion of cyclohexyl, cis- and trans-4-t-butylcyclohexyl, and cis- and trans-2-methylcyclohexyl nitrenoformates have been studied.The nitrenes were generated by vapour-phase (spray) pyrolysis or solution thermolysis of the corresponding azides, or by photolysis of tetrachlorothienyl S,N-ylides derived from the azides.The product ratios were principally (and predictably) dependent upon reaction temperatures (and thus conformational equilibria), these varying in the range 10-500 deg C. 17-Substituted esterone-derived nitrenoformates inserted either into the 12β (from 17β) or 14 α (from 17α) CH sites while 17-derivatives with the nitrene on the end of a long inert group abstracted hydrogen from the streoid B-ring.
