Journal of Synthetic Organic Chemistry, Japan
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
Studies on Heteroaromaticity. II.
Reactions of Furan Aldoxime Derivatives.
Tadashi SASAKIToshiyuki YOSHIOKA
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1967 Volume 25 Issue 8 Pages 665-671

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Abstract
The reactions of Anti- and syn-isomers of f uran- and 5-nitrof uran-aldoximes were studied; these are (1) addition reactions tof isocyanates, (2) substitution reactions with acryloyl chloride in the presence of triethylamine, and (3) rearrangement reactions with the aid of zinc chloride or polyphosphoric acid at 120°C-130°C. Furan- and 5-nitrofuran-hydroxymic acid chlorides were obtained from the corresponding aldoximes and nitrosyl chloride in absolute ether at -20°C. The latteracid chloride was treated with a primary or secondary amine to give an aminoxime which was in tautomerism with its aminoalcoholic form. The former, however, gave only furoxan, dimer of the nitriloxide, under the same conditions. Severalother reactions involving the above mentioned hydroxymic acid chlorides were also studied.
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© The Society of Syhthetic Organic Chemistry, Japan
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