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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.