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首页> 外文期刊>Bulletin of the Chemical Society of Japan >Reactivities of Stable Rotamers. XLIII. Diazotization of 2-Methyl-2-(1,2,3,4-tetrachloro- and 1,4-dimethoxy-9-triptycyl)propylamine Rotamers
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Reactivities of Stable Rotamers. XLIII. Diazotization of 2-Methyl-2-(1,2,3,4-tetrachloro- and 1,4-dimethoxy-9-triptycyl)propylamine Rotamers

机译：稳定转子的反应性。 XLIII。 2-甲基-2-（1,2,3,4-四氯-和1,4-二甲氧基-9-三苯甲基）丙胺旋转胺的重氮化

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摘要

The title amines were prepared from the corresponding rotamers of carboxylic acids via azides and isocyanates. Diazotization of these amines with isopentyl nitrite and organic acids commonly afforded olefins, that are derived from Wagner-Meerwein type rearrangement of the intervening cation followed by deprotonation. Other products included a cyclic compound derived by the attack of the carbocation on an unsubstituted benzeno bridge and esters derived from the acid which was used for diazotization. These two compounds are the products from the cation prior to the rearrangement. The sc-tetrachloro compound afforded the esters of the organic acids as almost an exclusive product and the sc-dimethoxy compound afforded a cyclized compound which is derived from the nucleophilic reaction of the 1-methoxy group with the cation, followed by demethylation of the resulting oxonium ion. These features are attributed to the strong interaction of the 1-substituent with the intermediate carbocations. In agreement with this interpretation, the formation of the corresponding ester is decreased with decreasing the nucleophilicity of the acid used for the diazotization of the sc-tetrachloro compound.
机译：由相应的羧酸旋转异构体通过叠氮化物和异氰酸酯制备标题胺。这些胺用亚硝酸异戊酯和有机酸进行重氮化通常可得到烯烃，这些烯烃是由居间阳离子的Wagner-Meerwein型重排衍生，然后进行去质子化。其他产品包括通过碳阳离子攻击未取代的苯甲醚桥而得到的环状化合物，以及衍生自用于重氮化的酸的酯。这两种化合物是重排之前来自阳离子的产物。所述sc-四氯化合物提供几乎作为排他性产物的有机酸的酯，所述sc-二甲氧基化合物提供了一种环化的化合物，其衍生自1-甲氧基与阳离子的亲核反应，然后将所得的产物脱甲基。氧离子。这些特征归因于1-取代基与中间碳阳离子的强烈相互作用。与该解释一致，随着用于sc-四氯化合物的重氮化的酸的亲核性降低，相应的酯的形成减少。

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