2--Hydroxyalkyl- and 2,7-Di(-hydroxyalkyl)-1,8-bis(dimethylamino

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• 作者：Alexander F. Pozharskii ; Alexander V. Degtyarev ; Oksana V. Ryabtsova ; Valery A. Ozeryanskii ; Mikhail E. Kletskii ; Zoya A. Starikova ; Lucjan Sobczyk ; Alexander Filarowski
• 刊名：Journal of Organic Chemistry
• 出版年：2007
• 出版时间：April 13, 2007
• 年：2007
• 卷：72
• 期：8
• 页码：3006 - 3019
• 全文大小：641K
• 年卷期：v.72,no.8(April 13, 2007)
• ISSN：1520-6904

文摘

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A regular set of 2-(mages/gifchars/alpha.gif" BORDER=0>-hydroxymethyl)- and 2,7-di(mages/gifchars/alpha.gif" BORDER=0>-hydroxymethyl)-1,8-bis(dimethylamino)naphthaleneshas been prepared. Their X-ray, NMR, and IR studies have demonstrated that in tertiary mono-alcoholsthe orientation of free nitrogen electron pairs in crystals and solution corresponds to nonconventionalin/out conformers stabilized by O-H···N intramolecular hydrogen bonding. For tertiary 2,7-dialcohols,the superimposed equilibrating in/out-out/in nitrogen invertomers are observed in solution. Unlike this,primary and secondary mono- and dialcohols commonly exist in the in/in form, which is typical for theparent proton sponge and the majority of its derivatives.