14種類の代表的な構造をもつ有機過酸化物について,テトラヒドロフラン中での臭化フェニルマグネシウムとの反応及び酢酸中でのヨウ化アルカリによるヨウ素遊離反応における反応性を比較検討した.過酸化物はO-O結合の隣の炭素に酸素,窒素などのヘテロ原子が結合した構造を持つときに二つの試薬に対する反応性が大きく,ヘテロ原子の非共有電子対がマグネシウム,カリウム,ナトリウムなどの対カチオンに配位する効果が大きいことが推論された.このことから,過酸化物の構造を基礎にしてヨウ素滴定法の代表的な3方法又はそれぞれを基本とする改良法の中から最適の1方法を容易に選択する基準が提出できた.

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1) Benzo-(h)-quinoline-N-oxide m.p. 123°, is formed when benzo-(h)-quinoline is heated with hydrogen peroxide and glacial acetic acid above 100°. Refluxion of this compound with acetic anhydride yields 2-hydroxybenzo-(h)-quinoline, m.p. 256°.
2) Benzo-(h)-quinoline-N-oxide gives a 2-cyano derivative, m.p. 161-162°, by the Reissert reaction, and is hydrolyzed to 2-carboxyl derivative, m.p. 181-182°.
3) Benzo-(h)-quinoline-N oxide differs from other aromatic amine-N-oxides in that it is partially reduced by SO₂ gas to yield a small amount of benzo-(h)-quinoline.
4) Nitration of 2-hydroxybenzo-(h)-quinoline gives 7-nitro derivative.

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The oxidation of organic compounds is not only a main source of available energy, but includes very important reactions for us concerning industrial chemistry, biology, medical science, and also environmental conservation, so that the studies on the oxidation reactions have been widely carried out from the early date of chemistry and still many active chemists are centering their interest on this reaction.
The present article reviews valuable and interesting studies reported in recent years on the organic oxidation with chemical oxidants beside molecular oxygen including studies carried out in our laboratory. The oxidation with molecular oxygen would be described by other authors in this symposium. Because of the limited pages we excluded electrolytic and biological oxidations and oxidations by organic compounds.
The present review is classified according to the oxidants as follows : heavy metal salts (Cr, Mn, Os, Xe, Co, Pd, Tl, Ru, and U salts), halogens and hypohalites (dark and photochemical reactions), hydrogen peroxide (under irradiation, base-catalyzed and heavy metal-catalyzed reactions), and miscellaneous peroxides (perphosphoric acid, peroxidiphosphate, alkyl hydroperoxides, and oxaziridines).

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A new reaction of hydroxylamine was found from a reaction between quinazoline and hydroxylamine and the structure of this reaction product, quinazoline 3-oxide (III) was determined in a following manner. (1) Reduction of (III) with palladiumcarbon affords tetrahydropyrimidoquinazoline and this reduction indicates the presence of an easily reducible oxygen which is not in the hydroxyl group of the hydroxy compound of quinazoline. This points to the fact that (III) is an N-oxide of quinazoline. (2) Oxidation of (III) with hydrogen peroxide affords 4-quinazoline 3-oxide (IV). (3) The position of the N-oxide group was determined from the fact that the alkaline hydrolysis of ethiodide, obtained from (III) and ethyl iodide, affords o-ethylarinobenzaldehyde oxime. (4) Quinazoline 3-oxide was prepared by the reacion of o-aminobenzaldehyde oxime and ethyl orthoformate.
Derivation of quinazoline to its N-oxide by the usual method failed to form the objective and 4-quinazolone was obtained in a quantitative yield.

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