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Volumn , Issue 9, 2007, Pages 1458-1460

A novel isocyanide-based three-component condensation reaction: Synthesis of fully substituted imino- and spiroiminocyclopentenes

(4) Shaabani, Ahmad a Rezayan, Ali Hossein a Rahmati, Abbas a Sarvary, Afshin a

a SHAHID BEHESHTI UNIVERSITY (Iran)

Author keywords

7,7,8,8 tetracyanoquinodimethane; Iminocyclopentene; Isocyanides; Spiroiminocyclopentene; Tetracyanoethylene

Indexed keywords

7,7,8,8 TETRACYANOQUINODIMETHANE; CARBOXYLIC ACID DERIVATIVE; CYCLOALKENE; DIACETYLENEDICARBOXYLATE DERIVATIVE; DICHLOROMETHANE; IMINE; IMINOCYCLOPENTENE; ISOCYANIDE DERIVATIVE; NITRILE; SPIROIMINOCYCLOPENTENE; TETRACYANOETHYLENE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 34250744227 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-980364 Document Type: Article

Times cited : (29)

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- Typical Procedure for the Preparation of Dimethyl 5-(tert-Butylimino)-3,3,4,4-tetracyanocyclopent-1-ene-1,2-dicarboxylate (4a) To a magnetically stirred solution of tetracyanoethylene (0.128 g, 1.0 mmol) and dimethylacetylenedicarboxylate (0.140 g, 1.0 mmol) in CH2Cl 2 (15 mL) was added dropwise a mixture of tert-butyl isocyanide (0.83 g, 1 mmol) in CH2Cl2 (2 mL) at -10°C over 10 min. The mixture was allowed to warm to r.t. and was stirred for 15 h. After completion of the reaction, the solvent was removed under vacuum and the residue was crystallized from CH2Cl2-n-hexane (1:2) to yield 0.353 g of 4a as a cream powder (100, mp 161-162°C. IR (KBr, νmax, 2256, 2207, 1739 cm-1. 1H NMR (300 MHz, CDCl3, δ, 1.56 [s, 9 H, CH3) 3C, 3.96 (s, 3 H, OCH3, 4.06 s, 3 H, OCH3
- 4: C, 67.92; H, 4.01; N, 14.67. Found: C, 67.46; H, 3.87; N, 15.40.

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