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Dithiane chemistry. III. The addition of Grignard reagents to substituted ketene dithioacetals.

โœ Scribed by Niels H. Andersen; Patrick F. Duffy; Alan D. Denniston; Douglas B. Grotjahn


Publisher
Elsevier Science
Year
1978
Tongue
French
Weight
255 KB
Volume
19
Category
Article
ISSN
0040-4039

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โœฆ Synopsis


The dithianylidene function (I) is well suited as a trap for anionic, cationic, and radical agents due to the ability of sulfur atoms to stabilize all three classes of carbon provalency.

2 The use of this function as an internal quench for carbocationic cyclizations, and studies of cyclizations initiated by the formation of dithienium cations (II)1a'3 illustrate the electrophilic end of this reaction spectrum. Although the anionic side was recognized


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Ketene dithioacetals III: the conjugate
โœ Frederick E. Ziegler; Coretta Chan Tam ๐Ÿ“‚ Article ๐Ÿ“… 1979 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 205 KB

The reilutive amounts of 1,2 to 1,4 addition products of severa ketene dithioacetal anions to cycZic a,B-unsaturated ketones have been determined. The influence of solvent and counterion is reported. Methods have been reported recently which permit the aprotic 1,4 addition of dithiane anions to a,@u

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The dithiane synthesis of carbonyl compounds, as developed by Corey and coworkers , involves the conversion of the potential carbonyl carbon into a reactive 2-lithio-1,3-dithiane. We have