A Novel Rearrangement of Arylvinylidenecyclopropanes to Naphthalene Derivatives Catalyzed by Lewis Acids or Brønsted Acids

Guang-Cai Xu; Ming Ma; Le-Ping Liu; Min Shi

doi:10.1055/s-2005-871565

LETTER

A Novel Rearrangement of Arylvinylidenecyclopropanes to Naphthalene Derivatives Catalyzed by Lewis Acids or Brønsted Acids

Guang-Cai Xu^a, Ming Ma^a, Le-Ping Liu^b, Min Shi*^a
^a School of Chemistry & Pharmaceutics, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. China
Fax: +86(21)64166128; e-Mail: Mshi@pub.sioc.ac.cn;
^b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, P. R. China

Abstract

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Abstract

Arylvinylidenecyclopropanes undergo a novel rearrangement in the presence of Lewis acids or Brønsted acids to give the corresponding naphthalene derivatives in good to high yields under mild conditions.

Key words

arylvinylidenecyclopropanes - Lewis acids - Brønsted acids - naphthalene derivatives - rearrangement

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Referenzen

References

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7

The ¹H and ¹³C NMR spectral data and analytic data of the compounds shown in Tables [1] and [2] and Scheme [2] , and detailed experimental procedures for their preparation, are available upon request from the author.

The high-level ab initio calculations predict the heats of formation of these 1-cyclopropylvinyl cations A-1, A-2, and A-3 to be 238.6, 242.5, and 256 kcal mol^-1, respectively; thus, initial protonation might take place to give the most thermodynamically stable cationic intermediate A-1 (Figure 1):

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10

Typical reaction procedure for the rearrangement of diarylvinylidenecyclopropanes: To a solution of diarylvinylidenecyclopropane 1d (64 mg, 0.2 mmol) in DCE (2.0 mL) was added Sn(OTf)₂ (8 mg, 0.02 mmol), the reaction mixture was stirred for 10 h at 80 °C (monitored by TLC). After the starting materials (diarylvinylidenecyclo-propans 1) were consumed, the solvent was removed under reduced pressure and the residue was subjected to flash column chromatography to give the desired product 2d (58 mg, 91%) as a colorless liquid. 2-Methyl-1-phenyl-4-(para-methylphenyl)-7-methylnaphthalene (2d): colorless oil; IR (CH₂Cl₂): 3053, 3023, 2954, 2923, 2855, 1620, 1600, 1516, 1507, 1440, 1381, 1362, 1029, 883, 824, 760, 703, 526 cm^-1; ¹H NMR (300 MHz, CDCl₃): δ = 2.22 (3 H, s, CH₃), 2.34 (3 H, s, CH₃), 2.45 (3 H, s, CH₃), 7.15-7.22 (2 H, m, Ar), 7.28-7.31 (5 H, m, Ar), 7.40-7.53 (5 H, m, Ar), 7.82 (1 H, d, J = 8.7 Hz, Ar); ¹³C NMR (75 MHz, CDCl₃): δ = 20.9, 21.3, 21.8, 125.4, 125.8, 126.9, 126.9, 128.4, 128.4, 128.8, 128.9, 130.0, 130.2, 132.7, 133.4, 135.2, 136.8, 137.0, 138.0, 139.2, 140.0; MS (EI): m/z (%) = 322 (100) [M⁺], 307 (10.3), 292 (7.6), 229 (3.8), 215 (5.1), 91 (1.7); HRMS (MALDI): m/z calcd for C₂₅H₂₃ (M⁺ + 1), 323.1794; found, 323.1786.