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triphenylmethanol : ウィキペディア英語版
triphenylmethanol

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Triphenylmethanol (also known as triphenylcarbinol, TrOH) is an organic compound. It is a white crystalline solid that is insoluble in water and petroleum ether, but well soluble in ethanol, diethyl ether, and benzene. In strongly acidic solutions, it produces an intensely yellow color, due to the formation of a stable "trityl" carbocation. Many derivatives of triphenylmethanol are important dyes.
==Structure and Properties==
Triphenylmethanol contains three phenyl rings and an alcohol group bound to a central tetrahedral carbon atom. All three C-Ph bonds are typical of ''sp''3-''sp''2 carbon-carbon bonds with lengths of approximately 1.47 Å, while the C-O bond length is approximately 1.42 Å.〔''Guidebook to Mechanism in Organic Chemistry'', Sixth Edition, 1996, Peter Sykes, ISBN 0-582-44695-3〕
The presence of three adjacent phenyl groups confers special properties manifested in the reactivity of the alcohol. For example it reacts with acetyl chloride, not to give the ester, but triphenylmethyl chloride:
:Ph3COH + MeCOCl → Ph3CCl + MeCO2H
The three phenyl groups also offer steric protection. Reaction with hydrogen peroxide gives an unusually stable hydroperoxide, Ph3COOH.〔Bryant E. Rossiter and Michael O. Frederick "Triphenylmethyl Hydroperoxide" E-EROS Encyclopedia of Reagents for Organic Synthesis, 2013. 〕

抄文引用元・出典: フリー百科事典『 ウィキペディア(Wikipedia)
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