RITTER REACTIONS .8. INCLUSION-COMPOUNDS FORMED BETWEEN N-(5H-DIBENZO[A,D]CYCLOHEPTYL)ACETAMIDES AND DIOXANE

被引：6

作者：

PICH, KC ^{[1
]}

BISHOP, R ^{[1
]}

CRAIG, DC ^{[1
]}

SCUDDER, ML ^{[1
]}

机构：

[1] UNIV NEW S WALES,SCH CHEM,SYDNEY,NSW 2052,AUSTRALIA

来源：

JOURNAL OF INCLUSION PHENOMENA AND MOLECULAR RECOGNITION IN CHEMISTRY | 1994年 / 18卷 / 02期

关键词：

AMIDE HOSTS; DIOXANE; HYDROGEN BONDING; RITTER REACTION; -C-H-CENTER-DOT-CENTER-DOT-CENTER-DOT-O-HYDROGEN BONDS;

D O I：

10.1007/BF00705818

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

5H-Dibenzo[a, d]cyclohepten-5-ol 2 and its saturated analogue 4 undergo Ritter reactions with acetonitrile and sulfuric acid to afford the acetamide derivatives 3 or 5 respectively. Both products form unstable inclusion compounds when crystallised from dioxane. The crystal structure of the dioxane compound of 3 is reported, This material [(C17H15NO).(C4H8O2)(2), Pnma, a = 9.616(1), b = 23.280(2), c = 10.298(1) Angstrom, Z = 4, R = 0.054] has the amide molecules arranged in parallel chains by means of intermolecular -N-H...O=C hydrogen bonds. The inclusion compound is stabilised by means of -C-H...O- hydrogen bonds. Each dioxane molecule is involved in five such interactions to neighbouring molecules of 3 and dioxane.

引用

页码：149 / 160

页数：12

共 13 条

[1] FLOW-VACUUM PYROLYSIS OF POLYCYCLIC COMPOUNDS .8. PYROLYSIS OF 5H-DIBENZO[A,D]CYCLOHEPTENE AND 10,11-DIHYDRO-5H-DIBENZO[A,D]CYCLOHEPTENE
BANCIU, MD
ENESCU, R
CIRA, O
BANCIU, A
PETRIDE, A
REVUE ROUMAINE DE CHIMIE, 1994, 39 (12) : 1449 - 1455
[2] Ritter reactions. IX. Transannular addition of nitriles to the 5H-dibenzo[a,d]cycloheptene ring system
Pich, Kim C.
Bishop, Roger
Craig, Donald C.
Scudder, Marcia L.
Australian Journal of Chemistry, 1994, 47 (05)
[3] RITTER REACTIONS .9. TRANSANNULAR ADDITION OF NITRILES TO THE 5H-DIBENZO[A,D]CYCLOHEPTENE RING-SYSTEM
PICH, KC
BISHOP, R
CRAIG, DC
SCUDDER, ML
AUSTRALIAN JOURNAL OF CHEMISTRY, 1994, 47 (05) : 837 - 851
[4] Inclusion Compounds of 5-(4-Methylphenyl)-5H-dibenzo[a,d]cyclohepten-5-ol with Dimethylsulphoxide, Morpholine and N-Methyl-2-pyrrolidinone
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Bissa, Marie L. Tangouna Liambo
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[5] Inclusion Compounds of 5-(4-Methylphenyl)-5H-dibenzo[a,d]cyclohepten-5-ol with Dimethylsulphoxide, Morpholine and N-Methyl-2-pyrrolidinone
Ayesha Jacobs
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[6] Ritter reactions .11. The diverse reactivity of 5,10-(azenometheno)-5H-dibenzo[a,d]cyclohepten-11-yl amides with dimethyl acetylenedicarboxylate
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[7] N-(5-Nitropyridin-2-yl)-5H-dibenzo[d,f][1,3]diazepine-6-carboxamide
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[8] TRIARYLMETHANOL HOSTS AND ANALOGS .8. CLATHRATE DESIGN FOR DIOXANE INCLUSION INVOLVING SINGLY BRIDGED TRIARYLMETHANOL HOSTS - SYNTHESIS, X-RAY CRYSTAL-STRUCTURES AND THERMAL STABILITIES OF 5 INCLUSION-COMPOUNDS
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ERTAN, A
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[9] N-(4-methylpyridin-2-yl)-5H-dibenzo[d,f][1,3]diazepine-6-carboxamide toluene hemisolvate
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ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2007, 63 : O4115 - U3660
[10] Synthesis, X-Ray, Hirshfeld Surface, DFT, and Molecular Docking Investigation of N-(5H-Dibenzo[a,d][7]Annulen-5-Ylidene)-2-Methylpropane-2-Sulfinamide
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