Synthesis of 3-Phenylsulfanyl-1,2-dihydronaphthalenes from Methylene­cyclopropanes and Benzenethiol

Lei Yu; Xian Huang; Minghua Xie

doi:10.1055/s-2006-926268

LETTER

Synthesis of 3-Phenylsulfanyl-1,2-dihydronaphthalenes from Methylenecyclopropanes and Benzenethiol

Lei Yu^a, Xian Huang*^a,b, Minghua Xie^a
^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 methylenecyclopropanes and benzenethiol in the presence of azobisisobutyronitrile gave 3-phenylsulfanyl-1,2-dihydronaphthalenes selectively.

Key words

methylenecyclopropanes - benzenethiol - radicals - radical reactions

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Referenzen

References

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13a

General Methods for the Synthesis of 3-Phenyl-sulfanyl-1,2-dihydronaphthalenes ( 9).
Under a nitrogen atmosphere, a solution of AIBN (0.3 mmol) and benzenethiol (0.3 mmol) in toluene (10 mL) was dropped very slowly into a solution of 1a (0.3 mmol) in toluene (10 mL) for 2 h at 110 °C and then kept at this temperature for 30 min. Then the solvent was evaporated under vacuum and the residue was subjected to preparative TLC (eluent: PE) to afford the product 9a (70 mg, 74%).

13b

Selected Data for 9a. Oil. ¹H NMR (400 MHz, CDCl₃): δ = 6.71-7.49 (m, 14 H), 2.94 (t, J = 8.0 Hz, 2 H), 2.57 (t, J = 8.0 Hz, 2 H). ¹³C NMR (100 MHz, CDCl₃): δ = 29.3, 29.4, 126.2, 126.6, 126.8, 127.2, 128.1, 128.7, 129.5, 129.9, 130.8, 132.0, 134.9, 135.1, 136.1, 138.9. IR (KBr): 2926, 2358, 1648, 1475, 1075, 745, 700 cm^-1. MS (EI, 70 eV): m/z (%) = 314 (100) [M⁺], 315 (32) [M + H⁺], 203 (44).

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Synthesis of 3-Phenylsulfanyl-1,2-dihydronaphthalenes from Methylene­cyclopropanes and Benzenethiol

Synthesis of 3-Phenylsulfanyl-1,2-dihydronaphthalenes from Methylenecyclopropanes and Benzenethiol