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6
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84914272780
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The addition of 1 molar equivalent of methyllithium to dichloro(2-chloroethyl)methylsilane (ether, 0° C.) yielded chloro(2-chloroethyl)dimethylsilane, b.p. 35-37° C. (10 mm Hg). [tends to decompose to dichlorodimethylsilane and ethene upon heating above 50° C.].
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7
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0001113382
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Yields were improved by using HMPA as a cosolvent. We are grateful to Dr. Howard E. Morton of Abbott Laboratories for suggesting the use of this solvent.
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(1984)
Tetrahedron Lett.
, vol.25
, pp. 495
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Corey1
Gross2
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8
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84914272779
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1HNMR analysis (ref. 6), then diluted with dry THF (∼10 mmole per mmole of starting enol ether), then a 4-fold excess of methyllithium (1.4 M solution in ether) was added. The mixture was stirred under nitrogen for 3 hours at room temperature, then carefully mixed with water and worked up in the usual manner to yield the crude alcohols.
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9
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84914272778
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2 of the ethyldimethylsilyl enol ether byproduct]; g) appearance of a new singlet at 0.2 ppm [methyl groups on silicon in the ethyldimethylsilyl enol ether byproduct]. Relative integrations of the [[Truncated]]
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10
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0002585940
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Previous approaches to 1-oxa-2-silacyclohexanes and discussions of their propensities to polymerize under protic conditions:
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(1974)
J. Organometallic Chem.
, vol.81
, pp. 33-40
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Smith1
Gooden2
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18
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33845373649
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In an attempt to minimize the amounts of tin byproducts produced, a “catalytic” recipe, after that of, could be used. However, the results from this method were virtually identical to those obtained from the “stoichiometric” recipe, and the oxasilacyclohexanes still could not be isolated from the reaction mixture.
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(1986)
J. Am. Chem. Soc.
, vol.108
, pp. 303
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Stork1
Sher2
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19
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84914272777
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Each alcohol was purified by flash chromatography (90:10 hexanes:ethyl acetate eluent). In the cases of products 13 and 14, diastereomer ratios were determined by HPLC analysis prior to purification. Each alcohol exhibited NMR and IR spectroscopic properties commensurate with the assigned structure, and upon analysis by high-resolution mass spectrometry gave molecular ion peaks and/or fragment ion peaks diagnostic for the assigned formula.
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21
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0001279669
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Recent accounts of the “reductive cyclizations” of 6-hepten-2-one systems, and similar freeradical cyclizations
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(1988)
J. Am. Chem Soc.
, vol.110
, pp. 5900
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Curran1
Kim2
Liu3
Shen4
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28
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84914272776
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This research was made possible by a grant from the donors of the Petroleum Research Fund, administered by the American Chemical Society (grant # 19870-ACl). The NMR spectrometer employed was purchased using funds provided by the National Science Foundation (#CHE-851404). RRK and NUO each thank the Graduate School of Texas Tech University for a Summer Research Award.
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