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The cycloaddition of heterocumulenes to oxetanes in the presence of catalytic amounts of tetraphenylstibonium iodide
Author(s) -
Fujiwara Masahiro,
Baba Akio,
Matsuda Haruo
Publication year - 1989
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.5570260628
Subject(s) - chemistry , cycloaddition , iodide , catalysis , cleavage (geology) , medicinal chemistry , ring (chemistry) , methyl iodide , organic chemistry , geotechnical engineering , fracture (geology) , engineering
Abstract The cycloadditions of carbon dioxide, isocyanates and carbodiimides to oxetanes proceeded in the presence of catalytic amounts of tetraphenylstibonium iodide ( 1 ) under mild conditions, affording the corresponding six‐membered heterocycles; 1,3‐dioxan‐2‐ones, 1,3‐oxazin‐2‐ones and 1,3‐oxazin‐2‐imines in good yields, respectively. Moreover, the cycloaddition of 2‐phenyloxetane proceeded via predominant ring‐cleavage at substituted site.