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Volumn , Issue 18, 2007, Pages 2871-2874

Study on the electrophilic tellurolactonization of 1,2-allenic phosphonates: A facile and efficient synthesis of 4-(phenyltelluro)-1,2- oxaphosphol-3-ene 2-oxides

(4) Yuan, Jingqi a Ruan, Xiuxiu a Yang, Yewei a Huang, Xian a,b

a ZHEJIANG UNIVERSITY (China)

b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY (China)

Author keywords

1,2 Allenic phosphonates; Electrophilic; Phosphorus heterocycles; Tellurolactonization

Indexed keywords

1,2 ALLENIC PHOSPHONATE; 4 (PHENYLTELLURO) 1,2 OXAPHOSPHOL 3 ENE 2 OXIDE; PHOSPHONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ORGANIC CHEMISTRY; STEREOCHEMISTRY; SYNTHESIS;

EID: 36549062870 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-991082 Document Type: Article

Times cited : (11)

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- Typical Experimental Procedure: To a solution of diphenyl ditelluride (0.6 mmol) in anhyd MeOH (2 mL) was added dropwise a solution of Br2 (0.60 mmol) and MeOH (1.2 mL) under nitrogen atmosphere. The mixture was stirred at r.t. for 2 h. Then 1,2-allenic phosphonates 1 (1.0 mmol) in anhyd MeOH (2 mL) was added to the above PhTeBr solution with stirring, and the reaction mixture was heated to 55°C After the reaction was complete (2 h, the mixture was concentrated and the residue was purified by flash chromatography to afford 4-(phenyltelluro)-1,2-oxaphosphol-3-ene 2-oxides 2. Compound 2a: white solid; mp 148-150°C 1H NMR (400 MHz, CDCl3, δ, 7.85-7.87 (m, 2 H, 7.29-7.49 (m, 3 H, 5.59 (d, J, 30.3 Hz, 1 H, 3.69 (d, J, 11.9 Hz, 3 H, 1.61 (s, 3 H, 1.55 (s, 3 H, 13C NMR (100 MHz, CDCl3, δ, 156.5 (d, J, 15.1 Hz, 140.9, 130.2, 129.9, 117.3 d, J, 154
- +], 77(100), 102(76), 51(74), 43(53), 67(46).

43
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- CCDC 661519 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/ data_request/cif, or by emailing data_request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033.
- CCDC 661519 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/ data_request/cif, or by emailing data_request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033.

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