Selective α‐cleavage cycloaddition of oxiranes with heterocumulenes catalyzed by tetraphenylstibonium iodide | Zendy

Fujiwara Masahiro | Zendy; Baba Akio | Zendy; Matsuda Haruo | Zendy

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Selective α‐cleavage cycloaddition of oxiranes with heterocumulenes catalyzed by tetraphenylstibonium iodide

Author(s) -

Fujiwara Masahiro,

Baba Akio,

Matsuda Haruo

Publication year - 1988

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.5570250515

Subject(s) - chemistry , oxazolidine , iodide , cycloaddition , catalysis , cleavage (geology) , lewis acids and bases , organic chemistry , medicinal chemistry , geotechnical engineering , fracture (geology) , engineering

A catalytic amount of tetraphenylstibonium iodide ( 1 ) promoted unusual cycloadditions of oxiranes with isocyanates or carbodiimides, forming 3,4‐disubstituted oxazolidin‐2‐ones 2 and oxazolidin‐2‐imines 4 under very mild conditions, respectively. In particular, carbodiimides gave 4 exclusively. Either oxazolidine, 3,4‐disubstituted or 3,5‐disubstituted ones could be obtained independently from the same reactants by the compensatable use of 1 and organotin iodide‐Lewis base complexes as catalysts.

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