References
- Theobald , P. G. and Okamura , W. H. 1990 . J. Org. Chem. , 55 : 741
- Theobald , P. G. and Okamura , W. H. 1987 . Tetrahedron Lett. , 28 : 6565
- t-Butyl phenyl sulfoxide can also be obtained from the reaction of phenyl vinyl sulfoxide and t-BuLi (58% yield).1H-NMR (CDCl3): δ1.17(9H), 7.4–7.6 (5H). 13C-NMT (CDCl3): δ22, 55.7, 126.3 128.3, 131.1, 140.0
- Okamura , W. H. , Shen , G-Y. and Tapia , R. 1986 . J. Am. Chem. Soc. , 108 : 5018
- Shen , G.-Y. , Tapia , R. and Okamura , W. H. 1987 . J. Am. Chem. Soc. , 109 : 7499
- The chemical shifts (1H-NMR, 300MHz, CDCl3) at C1'-H and C3'-H respectively, of the hydrocarbons: δ 5.85 (d, 10.7 Hz) and 5.68 (dq, 15.0 and 6.8 Hz) for 2a; δ 5.87 (d, 10.5 Hz) and 5.71 (d, 15.6 Hz) for 6a; δ 5.86 (d, 10.6 Hz) and 5.64 (dd, 15.3 and 6.9 Hz) for 7a; δ 5.91 (d, 10.7 Hz) and 5.18 (dd, 17.1 and 1.8 Hz) for 8a. [note, also: δ 4.96 (dd, 10.3 and 2.3 Hz) for H3E' of 8a, δ 4.95 (d, 9.9 Hz) for H3E' of 8b]. Compound 7a is a new compound: 1H-NMR: (CDCl3) δ 0.99 (6H, C4'-2CH3, d, J-6.7 Hz), 1.05 (6H, C1-2CH3, s), 2.20 (2H, H4, t, J-6.3 Hz), 2.32 (1H, C4'-H, m), 4.67 (1H, HE of exo methylene, d, J-2.6 Hz), 5.05 (1H, HZ of exo methylene, m), 5.64 (1H, C3'-H, dd, J-15.3 Hz), 6.9 Hz), 5.86 (1H, C1'-H, d, J-10.6 Hz), 6.42 (1H, C2'-H, ddd, J-15.2 Hz, 10.6 Hz, 0.7 Hz). 13C-NMR: (CDCl3) δ 22.6, 23.4, 27.5, 31.3, 37.1, 37.8, 41.4, 112.6, 120.3, 125.4, 140.4, 146.2, 149.5. HRMS: m/z 204.1881 (calc. for C15H24 (M), 204.1878)
- As a control, treatment of triene sulfoxides, 1, 5a 5b with MeLi (2 equiv) in ether (−78 °C, 10 min) followed by MeOH quench and standard waterether work-up afforded quantitative recovery of starting sulfoxides (1H-NMR analysis of the crude material revealed the absence of reduced hydrocarbon 2a, 6a 7a, respectively).
- Eisch , J. J. and Kaska , W. C. 1966 . J. Am. Chem. Soc. , 88 : 2213 It should be noted that there have been previous reports of the precautions necessary to optimize levels of label incorporation in an organometallic reaction. See