References
- Lanthanides: Chemistry and Use in Organic Synthesis Kagan, H. B.;Namy, J. L.;Kobayashi, S.(ed.)
- Chem. Rev. no.99 Krief, A.;Laval, A.-M.
- J. Org. Chem. no.59 Molander, G. A.;Shakya, S. R.
- J. Am. Chem. Soc. no.115 Molander, G. A.;McKie, J. A.
- J. Org. Chem. no.62 Molander, G. A.;Harris, C. R.
- The structure of the 3-(3-hydroxypropyl)cyclohex-2-one (3) was unambiguously identified by comparing it with the authentic sample which was prepared according to the method reported in the literature
- J. Org. Chem. no.47 Godleski, S. A.;Valpey, Rr. S.
- J. Org. Chem. no.47 Becker, D.;Harel, Z.; Nagler, M.; Gillon, A.
- J. Am. Chem. Soc. no.111 Imamoto, T.;Takiyama, N.;Nakamura, K.;Hatajima, T.;Kamija, Y.
- Synth. Com-mun. no.22 Crimmins, M. T.;Dedopoulou, D.
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Tetrahedron
no.46
The spiro compound 2 was also identified by spectro-scopic method and comparing with the
$^1H$ and$^{13}C$ NMR, and DEPT data with those reported in the literature. Mid-dleton D. S.;Simpkins, N. S. - J. Org. Chem. no.56 Molander, G. A.;Mckie, J. A.
- Tetrahedron Lett. no.41 Kang, H.-Y.;Song, S.-E.
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Typical Procedure: 3-(3-Hydroxypropyl)cyclohex-2-enone. 3-(3-Iodopropoxy)cyclohex-2-enone (200 mg, 0.71 mmol) in THF (2.0 mL) was added dropwise to a solution of SmI2 (4.3 mmol) in THF/HMPA (10% v/v) at 0 °C under nitrogen atmosphere. After stirring for 30 min at 0 °C, the reaction mixture was quenched with Rochells salt solu-tion.
$^{10}$ Extraction with dichloromethane, drying$(MgSO_4)$ , and concentration followed by flash chromatography pro-vided the desired hydroxyketone as a colorless oil - Synth. Commun. no.27 Schwaebe, M. K.;Little, R. D.
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- ChemInform Abstract: Vinylogous Intramolecular Nucleophilic Acyl Substitution Reactions Mediated by Samarium(II) Iodide. vol.32, pp.15, 2001, https://doi.org/10.1002/chin.200115065