1,3‐Dipolar cycloadditions of alkyl azides with picryl isothiocyanate:Isolation of stable monoadducts | Zendy

L'Abbá Gerrit | Zendy; Brems Patrick | Zendy; Albrecht Ernestine | Zendy

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1,3‐Dipolar cycloadditions of alkyl azides with picryl isothiocyanate:Isolation of stable monoadducts

Author(s) -

L'Abbá Gerrit,

Brems Patrick,

Albrecht Ernestine

Publication year - 1990

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.5570270446

Subject(s) - chemistry , isothiocyanate , alkyl , adduct , picryl chloride , yield (engineering) , phenyl isothiocyanate , medicinal chemistry , organic chemistry , materials science , immune system , metallurgy , immunology , biology

Picryl isothiocyanate ( 4 ), prepared in a two‐step sequence from picryl chloride ( 2 ), reacts smoothly with alkyl azides to yield 4‐alkyl‐5‐picrylimino‐1,2,3,4‐thiatriazolines 5 which are stable below 100°. These adducts combine with isocyanates in a bimolecular process with loss of nitrogen, similar to the formation of phenylimino derivatives but different from that of sulfonyliminothiatriazolines.

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