4667-74-7Relevant articles and documents
Hydroxylamine and pseudoacyl systems: Pseudo-oximes
Daniels, Anna M.,Supinski, Megan A.,Kennedy, Daniel P.,Robinson, William D.,Valente, Edward J.
, p. 6 - 13 (2013)
Unhindered furan pseudoacyl chlorides react with hydroxylamine and a carbonate base to form oxidized cyclic N-hydroxyiminoimides. Thus, 3-chloroisobenzofuran-1-one forms 3-hydroximinoisoindolin-1-one (4) C 8H6N2O2. Molecules are nearly planar and E-secondary amides hydrogen-bond with oximes through N(H)...N 2.920 A and O(H)...O 2.720 A contacts, and form infinite chains. Mucochloryl chloride (2,3,4-trichlorodihydrofuran-1-one) forms a similar hydroxyiminoimide (5E)-3,4-dichloro-5-hydroxyiminopyrrol-2-one (6), C 4H2Cl2N2O2. However, opianic acid forms a mixture of mostly N-hydroxyphthalimide [6,7-dimethoxy-N- hydroxyisoindolin-1,3-dione (9)], C10H10N 2O2, with small amounts of open oxime carboxylate [potassium 2,3-dimethoxy-6-(N-hydroxymethanoyl)benzoate (8) C10H 10NO5K], and 2,3-dimethoxyphthalimide (10), C 10H9NO4. These results suggest an intermediate pseudo-oxime, and such a derivative has been made in quantitative yield in a dehydration resistant arylpyran pseudoacyl system. 3-Chloro-4,4- dimethylisobenzopyran-1-one reacts with two equivalents of hydroxylamine and a carbonate base to form 2-hydroxy-3-(hydroxyamino)-4,4-dimethyl-3H-isoquinolin-1- one (14), C11H13N2O3, a pseudo-oxime. Pairs of pseudo-oximes form four hydrogen-bonds in two complementary sets, with N(H)...O 3.008 A and O(H)...O 2.685 A. Molecules are also linked in chains by hydrogen-bonds with O(H)...O 2.696 A. These products have been characterized by spectroscopy and X-ray diffraction. Graphical Abstract: [Figure not available: see fulltext.].