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Volumn , Issue 18, 2007, Pages 2919-2921

Reaction of 1-cyclopropylallenes with phenylselenyl bromide: A highly efficient and stereoselective method for the preparation of 2-phenylselenyl-6- bromo-1,3-hexadienes

(3) Yu, Lei a Meng, Bo a Huang, Xian a,b

a ZHEJIANG UNIVERSITY (China)

b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY (China)

Author keywords

1,3 hexadiene; Allene; Cyclopropyl; Ionic reaction; Selenium

Indexed keywords

1 CYCLOPROPYLALLENE; 2 PHENYLSELENYL 6 BROMO 1,3 HEXADIENE; ALLENE DERIVATIVE; CYCLOPROPANE DERIVATIVE; PHENYLSELENYL BROMIDE; SELENIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 36549078539 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-991094 Document Type: Article

Times cited : (11)

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28
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- Preparation of 2-Phenylselenyl-3-phenyl-6-bromo-1,3-hexadiene (9a, Typical Procedure: 1-Phenyl-1-cyclopropylallene (3a; 0.33 mmol) was first dissolved in CH2Cl2 (1 mL) and the reaction was kept at 0°C under ice-bath cooling. Under a nitrogen atmosphere protection, a solution of phenylselenyl bromide (0.3 mmol) in CH2Cl2 (6 mL) was slowly added. The reaction proceeded very rapidly and the color of phenylselenyl bromide disappeared immediately. The reaction liquid was stirred for an extra 1 min. Then, the solvent was evaporated under vacuum and the residue was separated by preparation TLC (eluent: PE) to give 9a in 78% yield. The other 2-phenylselenyl-6-bromo-1,3-hexadienes could be prepared in the similar way. Selected Data of 9a: IR (film, 3056, 3024, 1597, 1440, 1126, 882, 762, 740, 694 cm-1. 1H NMR (400 MHz, CDCl 3, δ, 7.29-7.55 (m, 10 H, 5.88 t, J
- 17SeBr: 391.9679; found: 391.9675.

29
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- 22OSe: 358.0836; found: 358.0844.

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