40058-90-0Relevant academic research and scientific papers
Sodium Borohydride Reactions under Phase-Transfer Conditions: Reduction of Azides to Amines
Rolla, Franco
, p. 4327 - 4329 (1982)
Under phase-transfer catalysis (PTC) conditions organic azides are reduced to amines in high yields by aqueous sodium borohydride: aryl and arylsulfonyl azides give the corresponding amino derivatives at room temperature, while alkyl azides require more drastic conditions (80 deg C). tert-Butyl 2-azido-2-phenylacetate, after reduction at room temperature and acidic workup, gives phenylglycine in a 72percent overall yield.The PTC technique allows the conversion of alkyl chlorides, bromides, and methanesulfonates into pure primary amines via a one-pot procedure by reacting a mixture of the substrate and a PTC agent first with aqueous NaN3 and then with aqueous NaBH4.
Steric effect in the Darzens condensation
Bansal, Raj, K.,Shrama, Vino K.
, p. 521 - 523 (2007/10/02)
A series of α-substituted t-butyl β-phenylglycidates (VI and IX to XIII) derived from p-substituted benzaldehydes and t-butyl chloroacetate, t-butyl α-chloropropionate and t-butyl α-chloropropionate and t-butyl α-chlorophenylacetate have been prepared by
Acid mediated decarboxylation of glycidic acids: Normal and rearranged products
Bansal, R K,Sharma, V K
, p. 482 - 485 (2007/10/02)
Two α-substituted t-butyl phenylglycidic esters have been synthesized by the familiar Darzens condensation.Acid-catalysed decarboxylation of the glycidic acids afford a mixture of two carbonyl compounds in each case.The analysis of the reaction mixture has been accomplished by HPLC and the structure of the products have been confirmed by synthesis.The previously reported mechanism does not seem to fully explain the formation of all the products.We believe that the formation of an aldehyde or ketone is function of the stability of the carbocation formed at the α- or β-position.
