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Volumn , Issue 2, 2008, Pages 229-232

A facile access to medium- and large-size naphthalenacarbocycles via Lewis acid mediated ring-expansion reaction of bicyclic vinylidenecyclopropanes

Author keywords

Bicyclic vinylidenecyclopropanes; Lewis acids; Ring expansion

Indexed keywords

BICYCLIC VINYLIDENECYCLOPROPANE DERIVATIVE; CYCLOPROPANE DERIVATIVE; LEWIS ACID; NAPHTHALENACARBOCYCLE DERIVATIVE; NAPHTHALENE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 38849146337     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-1000844     Document Type: Article
Times cited : (20)

References (34)
  • 4
    • 0344732854 scopus 로고
    • Trost, B. M, Ed, Pergamon Press: New York
    • (b) Billington, D. C. In Comprehensive Organic Synthesis, Vol. 3; Trost, B. M., Ed.; Pergamon Press: New York, 1991, 413-433.
    • (1991) Comprehensive Organic Synthesis , vol.3 , pp. 413-433
    • Billington, D.C.1
  • 33
    • 38849131544 scopus 로고    scopus 로고
    • Typical Procedure for the Preparation of 2: To a solution of bicyclic vinylidenecyclopropanes (0.5 mmol) in anhyd CH2Cl 2 (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
    • 32: 356.2504; found: 356.2512.
  • 34
    • 38849145263 scopus 로고    scopus 로고
    • Spectral data for 2i: 1H NMR (400 MHz, CDCl 3, 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, J1, 3.7 Hz, J2, 18.0 Hz, 1 H, 4.08 (dd, J1, 1.8 Hz, J2, 17.8 Hz, 1 H, 3.98 (dd, J1, 2.9 Hz, J2, 12.4 Hz, 1 H, 3.87 (dd, J1, 3.0 Hz, J2, 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
    • +], 231 (100).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.