Nucleophilic displacement of hydroxyl by cyanide ion: evidence for neighbouring group participation in the hydrolysis of a ferrocenylmethyl cyanide

1968 ◽  
pp. 120a ◽  
Author(s):  
J. H. Peet ◽  
B. W. Rockett
Keyword(s):  
Cyanide Ion ◽  
Group Participation ◽  
Nucleophilic Displacement ◽  
Neighbouring Group Participation ◽  
Hydrolysis Of

Dihydrotestosterone with an Ammonium Centre in the Position 16β

1997 ◽  
Vol 62 (4) ◽  
pp. 656-664 ◽  
Author(s):  
Barbora Slavíková ◽  
Alexander Kasal ◽  
Miloš Buděšínský
Keyword(s):  
Quaternary Ammonium ◽  
Water Soluble ◽  
High Yield ◽  
Partial Hydrolysis ◽  
Amino Group ◽  
Alternative Synthesis ◽  
Group Participation ◽  
Neighbouring Group Participation ◽  
Hydrolysis Of

In an alternative synthesis of 17β-hydroxy-16β-(piperidin-1-yl)-5α-androstan-3-one (4), neighbouring group participation between a 17β-carbonyloxy group and the 16β-amino group was used and a high yield partial hydrolysis of 3β,17β-diacetoxy-16β-(piperidin-1-yl)-5α-androstane (11) was developed. Interference of the neighbouring group participation was also apparent in another 17β-acetoxy derivative - in oxidation of compound 12 to 13. Compound 4 was converted into water-soluble derivatives, i.e. quaternary ammonium derivatives 17 to 20.

scholarly journals Neighbouring Group Participation in the Methanolysis of a Vicinal Diepoxide

1999 ◽  
Vol 23 (6) ◽  
pp. 356-357
Author(s):  
James R. Hanson ◽  
Peter B. Hitchcock ◽  
Ismail Kiran
Keyword(s):  
Hydroxy Group ◽  
Group Participation ◽  
Neighbouring Group Participation

The tetracyanoethylene catalysed methanolysis of 17β-acetoxy-4β,5β:6α,7α-diepoxyandrostane afforded 17β-acetoxy-4α,7α-oxido-5β-hydroxy-6β-methoxyandrostane in which the methanolysis product of the 6α,7α-epoxide has participated in the cleavage of the 4β,5β-epoxide; the reaction is modified however by an adjacent 3β-hydroxy group.

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