Chemical transformation of tetraacetal tetraoxa-cages to aza-cages and amido-cages mediated by iodotrimethylsilane and the combination of chlorotrimethylsilane and sodium iodide in nitriles

被引：13

作者：

Chern, JH ^{[1
]}

Wu, HJ ^{[1
]}

机构：

[1] Natl Chiao Tung Univ, Dept Appl Chem, Hsinchu, Taiwan

来源：

TETRAHEDRON | 1998年 / 54卷 / 22期

关键词：

D O I：

10.1016/S0040-4020(98)00277-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An one-pot conversion of tetraacetal tetraoxa-cages la-e to aza-cages 2a-e mediated by iodotrimethylsilane in alkyl nitriles at 25 degrees C via the ring expansion compound 9 as the reaction intermediate was discovered. A Ritter-type reaction was proposed for the mechanism of this conversion. On the other hand, reaction of tetraacetal tetraoxa-cages 1 with Me3SiCl and NaI in nitriles at 25 degrees C gave the amido-cages 12. Conjugated nitriles and Lewis acids, such as TiCl4 or BF3 . OEt2 were found to be ineffective for the conversion of era-cages to aza-cages. The structures of 2a and chemical transformation product 16 were proven by X-ray analysis. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：5967 / 5982

页数：16

相关论文

共 51 条

[1] CHIRAL ACETALS IN ASYMMETRIC-SYNTHESIS [J].

ALEXAKIS, A ;

MANGENEY, P .

TETRAHEDRON-ASYMMETRY, 1990, 1 (08) :477-511

[2] ASYMMETRIC-SYNTHESIS VIA ACETAL TEMPLATES .3. ON THE STEREOCHEMISTRY OBSERVED IN THE CYCLIZATION OF CHIRAL ACETALS OF POLYOLEFINIC ALDEHYDES - FORMATION OF OPTICALLY-ACTIVE HOMOALLYLIC ALCOHOLS [J].

BARTLETT, PA ;

JOHNSON, WS ;

ELLIOTT, JD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (07) :2088-2089

[3]

Bishop R, 1991, COMPREHENSIVE ORGANI, P261

[4] ASYMMETRIC-SYNTHESIS VIA CHIRAL ACETAL TEMPLATES .7. FURTHER-STUDIES ON THE CYANATION REACTION - THE USE OF ACETALS DERIVED FROM DIOLS WITH ONE CHIRAL CENTER [J].

CHOI, VMF ;

ELLIOTT, JD ;

JOHNSON, WS .

TETRAHEDRON LETTERS, 1984, 25 (06) :591-594

[5] THE ORIGIN OF STEREOSELECTIVE OPENING OF CHIRAL DIOXANE AND DIOXOLANE ACETALS - SOLUTION STRUCTURE OF THEIR LEWIS ACID COMPLEXES [J].

DENMARK, SE ;

WILLSON, TM ;

ALMSTEAD, NG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (26) :9258-9260

[6] MECHANISTIC AND STEREOCHEMICAL DIVERGENCE IN THE ALLYLSILANE-ACETAL ADDITION-REACTION [J].

DENMARK, SE ;

WILLSON, TM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (09) :3475-3476

[7] STUDIES ON THE MECHANISM AND ORIGIN OF STEREOSELECTIVE OPENING OF CHIRAL DIOXANE ACETALS [J].

DENMARK, SE ;

ALMSTEAD, NG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (21) :8089-8110

[8] ON THE LEWIS ACID-INDUCED ADDITION OF ALLYLSTANNANES TO ALDEHYDES - A SPECTROSCOPIC INVESTIGATION [J].

DENMARK, SE ;

WILSON, T ;

WILLSON, TM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (03) :984-986

[9] ON THE STEREOSELECTIVE OPENING OF CHIRAL DIOXANE ACETALS - NUCLEOPHILE DEPENDENCE [J].

DENMARK, SE ;

ALMSTEAD, NG .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (23) :6485-6487

[10] ASYMMETRIC-SYNTHESIS VIA ACETAL TEMPLATES .5. REACTIONS WITH CYANOTRIMETHYLSILANE - ENANTIOSELECTIVE PREPARATION OF CYANOHYDRINS AND DERIVATIVES [J].

ELLIOTT, JD ;

CHOI, VMF ;

JOHNSON, WS .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (13) :2294-2295

← 1 2 3 4 5 6 →