Reaction of 1-Cyclopropylallenes with Phenylselenyl Bromide: A Highly Efficient and Stereoselective Method for the Preparation of 2-Phenylselenyl-6-bromo-1,3-hexadienes

Lei Yu; Bo Meng; Xian Huang

doi:10.1055/s-2007-991094

LETTER

Reaction of 1-Cyclopropylallenes with Phenylselenyl Bromide: A Highly Efficient and Stereoselective Method for the Preparation of 2-Phenylselenyl-6-bromo-1,3-hexadienes

Lei Yu^a, Bo Meng^a, Xian Huang*^a,b
^a Department of Chemistry, Zhejiang University (Campus Xixi), Hangzhou 310028, P. R. of China
^b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
Fax: +86(571)88807077; e-Mail: huangx@mail.hz.zj.cn;

Abstract

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Abstract

Reaction of 1-cyclopropylallenes with phenylselenyl bromide, which provided a highly efficient and stereoselective method for the preparation of 2-phenylselenyl-6-bromo-1,3-hexadienes, was investigated.

Key words

cyclopropyl - allene - selenium - 1,3-hexadiene - ionic reaction

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References

References and Notes

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1a Brandi A. Goti A. Chem. Rev. 1998, 98: 589

1b Brandi A. Cicchi S. Cordero FM. Goti A. Chem. Rev. 2003, 103: 1213

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2 Krause N. Hashmi ASK. Modern Allene Chemistry Wiley-VCH; Weinheim: 2004. and references therein

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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, CDCl₃): δ = 7.29-7.55 (m, 10 H), 5.88 (t, J = 6.8 Hz, 1 H), 5.63 (s, 1 H), 5.53 (s, 1 H), 3.32 (t, J = 7.2 Hz, 2 H), 2.78-2.83 (m, 2 H). ¹³C NMR (100 MHz, CDCl₃): δ = 32.2, 33.0, 118.2, 126.6, 126.9, 127.6, 127.9, 128.2, 128.6, 129.0, 136.6, 138.7, 139.8, 142.9. MS (EI, 70 eV): m/z (%) = 392 (26) [M⁺], 236 (22), 155 (100). HRMS (EI): m/z calcd for C₁₈H₁₇SeBr: 391.9679; found: 391.9675.

9

Spectral Data of Compound 11: IR (film): 2973, 2924, 1441, 1068, 1025, 740, 699 cm^-1. ¹H NMR (400 MHz, CDCl₃): δ = 7.28-7.59 (m, 10 H), 6.01 (s, 1 H), 5.09 (s, 1 H), 3.67-3.79 (m, 2 H), 1.54-1.57 (m, 1 H), 1.35 (t, J = 6.8 Hz, 3 H), 0.43-0.55 (m, 2 H), 0.14-0.24 (m, 2 H). ¹³C NMR (100 MHz, CDCl₃): δ = 0.7, 3.5, 15.7, 16.6, 58.4, 85.7, 115.1, 127.2, 127.3, 127.8, 128.2, 129.2, 129.3, 136.7, 140.0, 152.1. MS (EI, 70 eV): m/z (%) = 358 (5) [M⁺], 317 (26), 105 (100). HRMS (EI): m/z calcd for C₂₀H₂₂OSe: 358.0836; found: 358.0844.