TY - JOUR
T1 - The acid-catalysed reaction of thiols with alkyl 2,3-dideoxy-glyc-2-enopyranosides or glycals
AU - Priebe, Waldemar
AU - Zamojski, Aleksander
PY - 1980
Y1 - 1980
N2 - The acid-catalysed (HCl or SnCl4) reaction of alkyl 2,3 dideoxy-glyc-2-enopyranosides or 3,4,6-tri-O-acetyl-D-glycals with thiols leads to mixtures of alkyl 2,3-dideoxy-1-thio-glyc-2-enopyranosides and 3-S-alkyl-3-thioglycals. Under equilibrium conditions the latter are the preponderant products of the reaction. Cross experiments have confirmed the intermediacy of the allylic carbocation in the reaction. A rationalization of the substitution reactions of 1,2- and 2,3-unsaturated sugars based on HSAB principle has been proposed.
AB - The acid-catalysed (HCl or SnCl4) reaction of alkyl 2,3 dideoxy-glyc-2-enopyranosides or 3,4,6-tri-O-acetyl-D-glycals with thiols leads to mixtures of alkyl 2,3-dideoxy-1-thio-glyc-2-enopyranosides and 3-S-alkyl-3-thioglycals. Under equilibrium conditions the latter are the preponderant products of the reaction. Cross experiments have confirmed the intermediacy of the allylic carbocation in the reaction. A rationalization of the substitution reactions of 1,2- and 2,3-unsaturated sugars based on HSAB principle has been proposed.
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U2 - 10.1016/0040-4020(80)80017-2
DO - 10.1016/0040-4020(80)80017-2
M3 - Article
AN - SCOPUS:0000388697
SN - 0040-4020
VL - 36
SP - 287
EP - 297
JO - Tetrahedron
JF - Tetrahedron
IS - 2
ER -