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Amidrazones. 14. The formation of 1,1‐disubstituted hydrazines from the base‐promoted hydrolysis of 1,l‐disubstituted‐3‐amino‐4,5‐dihydro‐1 H ‐pyrazolium halides: Mechanistic considerations
Author(s) -
Smith Richard F.,
Dennis Lisa A.,
Ryan William J.,
Rodriguez George,
Brophy Keith A.
Publication year - 1992
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570290133
Subject(s) - chemistry , halide , hydrolysis , hydroxide , base (topology) , tetrahedral carbonyl addition compound , sodium hydroxide , ammonia , medicinal chemistry , ion , alkaline hydrolysis , combinatorial chemistry , organic chemistry , catalysis , mathematical analysis , mathematics , nucleophile
Three mechanistic pathways are considered for the hydroxide‐promoted conversion of 1,1‐disubstituted‐3‐amino‐4,5‐dihydro‐1 H ‐pyrazolium halides 1 to 1,1‐disubstituted hydrazines, ammonia and sodium 3‐hydroxypropanoate. Evidence presented in this paper supports a hydrolysis mechanism c that is initiated by hydroxide ion addition to the 3‐position of 1 to form a tetrahedral intermediate 7 .