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 | Zendy

Smith Richard F. | Zendy; Dennis Lisa A. | Zendy; Ryan William J. | Zendy; Rodriguez George | Zendy; Brophy Keith A. | Zendy

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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 .

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