peri-Naphthylenediamines -: 26.: Unexpected formation of naphtho[1,8-c,d]pyran derivatives in the reaction of 1,8-bis(dimethylamino) naphthalene with trifluoroacetic anhydride.: A new type of double naphthalene "proton sponges"

被引：11

作者：

Pozharskii, AF

Tregub, NG

Vistorobskii, NV

Romanova, EY

Starikova, ZA

Yanovsky, AI

机构：

[1] Rostov State Univ, Rostov Na Donu 344090, Russia

[2] Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 117813, Russia

来源：

RUSSIAN CHEMICAL BULLETIN | 1999年 / 48卷 / 07期

关键词：

1,8-bis(dimethylamino)naphthalene; proton sponge; naphtho[1,8-c,d]pyran; cis- and trans-diols; trifluoroacetic anhydride; C-acylation; covalent hydration; X-ray diffraction analysis; NMR spectra;

D O I：

10.1007/BF02495294

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The reaction of 1,8-bis(dimethylamino)naphthalene ("proton sponge") with trifluoroacetic anhydride afforded new derivatives of naphtho[1,8-c,d]pyran, viz., trans- (4) and cis-1,3-dihydroxy-6,7-bis(dimethylamino)-1,3-bis(trifluoromethyl)-1H,3H-naphtho[1,8-c,d]pyran (5) and symmetrical 3,4,10,11-tetrakis(dimethylamino)-7,14-bis(trifluoromethyl)-7,14-epoxy-dinaphtho[1,8-a,b; 1',8'-ef]cyclooctane (3), which belongs to a new type of double "proton sponges," along with the expected 1,8-bis(dimethylamino)-4-trifluoroacetylnaphthalene. The structures of compounds 3 and 4 were established by spectral studies and X-ray diffraction analysis.

引用

页码：1299 / 1309

页数：11

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