126647-40-3Relevant academic research and scientific papers
Studies of Substituent Effect in the Formation of Benzonitrile Oxides and 1,3-Dipolar Adducts of the Benzonitrile Oxides with 2,3,4,6-Tetra-O-acetyl-1-thio-β-D-glucopyranose
Saito, Setsuo,Uzawa, Hiroshi,Nagatsugi, Fumi
, p. 2519 - 2522 (2007/10/02)
Coupling reagents were prepared from corresponding benzaldehyde oximes by successive treatment with chlorine and Et3N; the products were used without purification because of their instability.The reactions of 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranose (1) with the coupling reagents obtained from benzaldehyde oxime (2a) and phenylacetaldehyde oxime (2b) gave normal 1,3-dipolar addition products (3a and 3b, respectively) in good yields.The reactions of 1 with the coupling reagents obtained from p- (2c), m- (2d), and o-methoxybenzaldehyde oxime (2e) gave the 1,3-addition products chlorinated on the benzene ring; 3c and 3d from 2c, 3e and 3f from 2d, and 3g from 2e.On the other hand, the reactions of 1 with the coupling reagents obtained from p-chloro- (2f) and p-nitrobenzaldehyde oxime (2g) gave no 1,3-addition product.Keywords - benzonitrile oxide; benzaldehyde oxime; coupling reagent; substituent effect; 1,3-dipolar addition reaction; 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranose
