Neighboring-group participation in carbohydrate chemistry. IV. Neighboring-group reaction of the 6-benzamido group in a nucleophilic displacement of a 5-mesylate

1973 ◽  
Vol 38 (4) ◽  
pp. 716-719 ◽  
Author(s):  
Momcilo Miljkovic ◽  
Toshio Satoh ◽  
Margaret Konopka ◽  
Eugene A. Davidson ◽  
Dusan Miljkovic
Keyword(s):  
Carbohydrate Chemistry ◽  
Neighboring Group ◽  
Group Participation ◽  
Nucleophilic Displacement ◽  
Group Reaction ◽  
Neighboring Group Participation

Neighboring-group participation in carbohydrate chemistry

1971 ◽  
Vol 17 (1) ◽  
pp. 155-164 ◽  
Author(s):  
M. Miljkovic´ ◽  
A. Jokic´ ◽  
E.A. Davidson
Keyword(s):  
Carbohydrate Chemistry ◽  
Neighboring Group ◽  
Group Participation ◽  
Neighboring Group Participation

Neighboring group participation in hypobromous acid addition to 19-substituted 5α-cholest-1-enes and in acid cleavage of their epoxy analogs

1982 ◽  
Vol 47 (11) ◽  
pp. 3062-3076 ◽  
Author(s):  
Václav Černý ◽  
Pavel Kočovský
Keyword(s):  
Neighboring Group ◽  
Group Participation ◽  
Acid Addition ◽  
Acid Cleavage ◽  
Hypobromous Acid ◽  
Neighboring Group Participation

Reactions of the title compounds (bearing an OH, OCH3 or OCOCH3 group at C(19)) involve 5(O)n, 7(O)π,n-participation by the 19-substituent or attack by an external nucleophile. The 6(O)π,n-participation does not occur. The behavior of 1,2-unsaturated (or epoxidated) compounds has been compared with the earlier described 2,3-unsaturated or epoxidated analogs. The 1,2-type is genarally less prone to participation. The reasons for this behavior are discussed.

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