Unexpected chlorination products as a result of self‐diazotization of three amino‐dinitro‐2,3,4,5‐tetrahydrobenzo[ b ][1,4]dioxocin Derivatives | Zendy

Takakis Ioannis M. | Zendy; Hadjimihalakis Phaedon M. | Zendy

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Unexpected chlorination products as a result of self‐diazotization of three amino‐dinitro‐2,3,4,5‐tetrahydrobenzo[ b ][1,4]dioxocin Derivatives

Author(s) -

Takakis Ioannis M.,

Hadjimihalakis Phaedon M.

Publication year - 1991

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.5570280703

Subject(s) - chemistry , nitrous acid , sodium nitrite , hydrochloric acid , ethylene glycol , organic chemistry , nitro , nitrite , alkyl , nitrate

Diazotization of the dinitroaryl amines 1 with nitrous acid (generated from hydrochloric acid and sodium nitrite) furnished the unexpected chloronitro azides 3 as a result of self‐diazotization. Subsequent heating of 3 in ethylene glycol afforded the corresponding chloro‐nitro amines 5 and/or the deaminated products 4 . Some mechanistic aspects of these transformations are discussed.

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