{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,14]],"date-time":"2025-10-14T06:47:04Z","timestamp":1760424424055,"version":"3.40.5"},"reference-count":31,"publisher":"American Chemical Society (ACS)","issue":"18","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Org. 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P.","year":"1995","author":"For","key":"ol026423ib00017\/ol026423ib00017_1"},{"key":"ol026423ib00018\/ol026423ib00018_1","first-page":"2644","volume":"35","author":"Pearson W. H.","year":"1994","journal-title":"Tetrahedron Lett."},{"key":"ol026423ib00018\/ol026423ib00018_2","first-page":"9827","volume":"63","author":"Pearson W. H.","year":"1998","journal-title":"J. Org. Chem."},{"unstructured":"Preparation of 12 and 14.n-Butyllithium (0.55 mL of a 2.38 M solution in hexanes, 1.3 mmol) was added in a dropwise fashion to a solution of the stannane11(0.391 g, 1.00 mmol) and cycloheptatriene (0.52 mL, 0.462 g, 5.0 mmol) in THF (4 mL) at \u221278 \u00b0C. After 30 min, saturated aqueous ammonium chloride was added and the mixture was diluted with ether. The organic layer was washed with water (three times) and brine, dried (Na2SO4), and concentrated. Chromatography (0\u221225% ethyl acetate\/hexanes gradient) gave 66.9 mg (35%) of12and 53.1 mg (28%) of14as clear colorless oils. Data for12:\u2009 Rf0.06 (25% ethyl acetate\/hexanes);1H NMR (500 MHz, C6D6)\u03b46.19 (dd, 1 H,J= 11.5, 7.5 Hz), 5.93 (ddt, 1 H,J= 11.5, 7.5, 1 Hz), 5.85 (ddt, 1 H,J= 11.5, 7.3, 1 Hz), 5.61 (dd, 1 H,J= 11.5, 7.0 Hz), 3.30 (s, 3 H), 3.25 (d, 1 H,J= 6.5 Hz), 2.66 (t, 1 H,J= 6.3 Hz), 2.04\u22121.85 (m, 5 H), 1.48 (app d, 1 H,J= 13.5 Hz), 1.40 (ddd, 1 H,J= 12.5, 10.5, 4.8 Hz), 1.23 (ddd, 1 H,J= 12, 10, 4 Hz);13C NMR (125 MHz, C6D6)\u03b4136.0, 135.9, 127.1, 126.6, 99.9, 61.4, 47.9, 46.7, 42.2, 28.6, 27.3, 24.0; IR (neat) 3309 (m), 1652 (w), 1594 (w) cm-1; MS (EI, 70 eV)m\/z(rel int) 191.1 (59, M+), 99.1 (64), 84 (100); HRMS (EI, 70 eV) calcd for C12H17NO (M+) 191.1310, found 191.1309. Data for14:\u2009 Rf0.37 (30% ethyl acetate\/hexanes);1H NMR (500 MHz, C6D6)\u03b46.01 (dm, 1 H,J= 11.5 Hz), 5.79\u22125.70 (m, 2 H), 5.65\u22125.60 (m, 1 H), 3.77 (q, 1 H,J= 7 Hz), 3.68 (s, 3 H), 2.86 (dm, 1 H,J= 20 Hz), 2.77\u22122.70 (m, 1 H), 2.63 (dt, 1 H,J= 20, 5.8 Hz), 2.33 (tm, 1 H,J= 5.8 Hz), 2.20\u22122.10 (m, 3 H), 1.73\u22121.64 (m, 1 H), 1.46\u22121.36 (m, 1 H);13C NMR (100 MHz, C6D6)\u03b4172.4, 134.5, 130.0, 128.2, 127.9, 71.2, 55.1, 43.7, 31.3, 29.9, 28.8, 27.7; IR (neat) 1650 (s) cm-1; MS (EI, 70 eV)m\/z(rel int) 191.3 (10), 176.3 (16), 98.2 (100), 84.1 (17), 70.1 (9); HRMS (EI, 70 eV) calcd for C12H17NO (M+) 191.1310, found 191.1312.","key":"ol026423ib00019\/ol026423ib00019_1"},{"key":"ol026423ib00020\/ol026423ib00020_1","doi-asserted-by":"crossref","first-page":"4777","DOI":"10.1021\/jo00043a046","volume":"57","author":"O'Connell J. F.","year":"1992","journal-title":"J. Org. 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