A Facile Access to Medium- and Large-Size Naphthalenacarbocycles via Lewis Acid Mediated Ring-Expansion Reaction of Bicyclic Vinylidenecyclopropanes

Xian Huang; Chenliang Su; Qingyang Liu; Yuetong Song

doi:10.1055/s-2007-1000844

LETTER

A Facile Access to Medium- and Large-Size Naphthalenacarbocycles via Lewis Acid Mediated Ring-Expansion Reaction of Bicyclic Vinylidenecyclopropanes

Xian Huang*^a,b, Chenliang Su^a, Qingyang Liu^a, Yuetong Song^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

Ring-expansion reactions of bicyclic vinylidenecyclopropanes in the presence of Lewis acid was investigated, providing an efficient method for the synthesis of naphthalenes with annulated carbocycles of various ring sizes in good to excellent yields under mild conditions.

Key words

bicyclic vinylidenecyclopropanes - ring expansion - Lewis acids

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References and Notes

<A NAME="RW18007ST-1A">1a</A> Breitenbach J. Boosfeld J. Vögtle F. In Comprehensive Supramolecular Chemistry Vol. 2: Lehn JM. Pergamon; New York: 1996. p.29-67

<A NAME="RW18007ST-1B">1b</A> Dietrich B. Viout P. Lehn JM. Macrocyclic Chemistry Wiley-VCH; Weinheim: 1993.

<A NAME="RW18007ST-2A">2a</A> Vögtle F. Brodesser G. Nieger M. Rissanen K. Recl. Trav. Chim. Pays-Bas 1993, 112: 325

<A NAME="RW18007ST-2B">2b</A> Billington DC. In Comprehensive Organic Synthesis Vol. 3: Trost BM. Pergamon Press; New York: 1991. p.413-433

<A NAME="RW18007ST-3">3</A> Schubert WM. Sweeney WA. Latourette HK. J. Am. Chem. Soc. 1954, 76: 5462

<A NAME="RW18007ST-4">4</A> Cram DJ. Gaston LK. J. Am. Chem. Soc. 1960, 82: 6386

<A NAME="RW18007ST-5">5</A> Takahashi S. Mori N. J. Chem. Soc., Perkin Trans. 1 1991, 2029

<A NAME="RW18007ST-6A">6a</A> Ma S. Negishi E. J. Am. Chem. Soc. 1995, 117: 6345

<A NAME="RW18007ST-6B">6b</A> Hildebrandt D. Hüggenberg W. Kanthak M. Plöger T. Müller M. Dyker G. Chem. Commun. 2006, 2260

<A NAME="RW18007ST-7A">7a</A> O’Keeffe S. Harrington F. Maguire AR. Synlett 2007, 2367

<A NAME="RW18007ST-7B">7b</A> Paquette LA. Sun L. Friedrich D. Savage PB. J. Am. Chem. Soc. 1997, 119: 8438

<A NAME="RW18007ST-7C">7c</A> Liu H. Shook CA. Jamison JA. Thiruvazhi M. Cohen T. J. Am. Chem. Soc. 1993, 120: 605

<A NAME="RW18007ST-7D">7d</A> Klapars A. Parris S. Anderson KW. Buchwald SL. J. Am. Chem. Soc. 2004, 126: 3529

<A NAME="RW18007ST-8A">8a</A> Brandi A. Goti A. Chem. Rev. 1998, 98: 598

<A NAME="RW18007ST-8B">8b</A> Nakamura I. Yamamoto Y. Adv. Synth. Catal. 2002, 344: 111

<A NAME="RW18007ST-8C">8c</A> Brandi A. Cicchi S. Cordero FM. Goti A. Chem. Rev. 2003, 103: 1213

<A NAME="RW18007ST-9A">9a</A> Huang X. Yang Y. Org. Lett. 2007, 9: 1667

<A NAME="RW18007ST-9B">9b</A> Yu L. Huang X. Xie M. Synlett 2006, 423

<A NAME="RW18007ST-9C">9c</A> Huang X. Yu L. Synlett 2005, 2953

<A NAME="RW18007ST-9D">9d</A> Zhou H. Huang X. Chen W. J. Org. Chem. 2004, 69: 5471

<A NAME="RW18007ST-10A">10a</A> Isagawa K. Mizuno K. Sugita H. Otsuji Y. J. Chem. Soc., Perkin Trans. 1 1991, 2283

<A NAME="RW18007ST-10B">10b</A> Mizuno K. Sugita H. Kamada T. Otsuji Y. Chem. Lett. 1994, 23: 449

<A NAME="RW18007ST-10C">10c</A> Mizuno K. Sugita H. Isagawa K. Goto M. Otsuji Y. Tetrahedron Lett. 1993, 34: 5737

<A NAME="RW18007ST-10D">10d</A> Mizuno K. Nire K. Sugita H. Otsuji Y. Tetrahedron Lett. 1993, 34: 6563

<A NAME="RW18007ST-10E">10e</A> Mizuno K. Maeda H. Sugita H. Nishioka S. Hirai T. Sugimoto A. Org. Lett. 2001, 3: 581

<A NAME="RW18007ST-10F">10f</A> Maeda H. Hirai T. Sugimoto A. Mizuno K. J. Org. Chem. 2003, 68: 7700

<A NAME="RW18007ST-10G">10g</A> Xu G.-C. Ma M. Liu L.-P. Shi M. Synlett 2005, 1869

<A NAME="RW18007ST-10H">10h</A> Xu G.-C. Liu L.-P. Lu J.-M. Shi M. J. Am. Chem. Soc. 2005, 127: 14552

<A NAME="RW18007ST-10I">10i</A> Zhang Y.-P. Lu J.-M. Xu G.-C. Shi M. J. Org. Chem. 2007, 72: 509

<A NAME="RW18007ST-10J">10j</A> Shao L.-X. Zhang Y.-P. Qi M.-H. Shi M. Org. Lett. 2007, 9: 117

<A NAME="RW18007ST-10K">10k</A> Liu L.-P. Lu J.-M. Shi M. Org. Lett. 2007, 9: 1303

<A NAME="RW18007ST-10L">10l</A> Lu J.-M. Shi M. Org. Lett. 2007, 9: 1805

Typical Procedure for the Preparation of 2: To a solution of bicyclic vinylidenecyclopropanes (0.5 mmol) in anhyd CH₂Cl₂ (3 mL) under N₂ was added TiCl₄ (28.4 mg, 0.15 mmol) under a nitrogen atmosphere. The mixture was stirred at r.t. for 2 h. After the reaction was complete, the mixture was concentrated and the residue was purified by flash chromatography to afford medium- and large-size naphthalenacarbocycles 2. Selected spectral data for 2h: ¹H NMR (400 MHz, CDCl₃): δ = 8.07 (d, J = 8.0 Hz, 1 H), 7.87 (d, J = 8.4 Hz, 1 H), 7.42-7.53 (m, 5 H), 7.36-7.42 (m, 1 H), 7.30-7.36 (m, 1 H), 7.25 (s, 1 H), 3.00-3.09 (m, 2 H), 2.70-2.80 (m, 2 H), 1.74-1.89 (m, 4 H), 1.64-1.73 (m, 2 H), 1.48-1.64 (m, 6 H), 1.34-1.48 (m, 6 H). ¹³C NMR (100 MHz, CDCl₃): δ = 23.2, 23.4, 24.5, 24.6, 26.4, 26.6, 26.9, 27.0, 27.1, 27.8, 32.3, 123.9, 124.5, 125.6, 126.6, 126.9, 128.1, 129.8, 130.2, 130.6, 132.8, 135.1, 137.4, 138.2, 141.1. IR (KBr): 2929, 2856, 1461, 1383, 762, 707 cm^-1. MS (70 eV, EI): m/z = 356 [M⁺], 356 (100). HRMS (EI): m/z [M⁺] calcd for C₂₇H₃₂: 356.2504; found: 356.2512.

Spectral data for 2i: ¹H NMR (400 MHz, CDCl₃): = 7.33-7.41 (m, 3 H), 7.27-7.32 (m, 7 H), 6.42 (s, 1 H), 5.57 (t, J = 2.6 Hz, 1 H), 4.24 (d, J = 2.2 Hz, 1 H), 4.17 (dd, J ₁ = 3.7 Hz, J ₂ = 18.0 Hz, 1 H), 4.08 (dd, J ₁ = 1.8 Hz, J ₂ = 17.8 Hz, 1 H), 3.98 (dd, J ₁ = 2.9 Hz, J ₂ = 12.4 Hz, 1 H), 3.87 (dd, J ₁ = 3.0 Hz, J ₂ = 12.4 Hz, 1 H). ¹³C NMR (100 MHz, CDCl₃): δ = 54.0, 65.5, 70.0, 125.1, 127.4, 127.5, 127.6, 128.1, 128.3, 129.8, 132.7, 140.0, 142.5, 143.9. IR (film): 3056, 3024, 2925, 2852, 1658, 1598, 1491, 1445, 1380, 1135, 1080, 758, 700 cm^-1. MS (70 eV, EI): m/z = 296 [M⁺], 231 (100).