- A RAPID, EFFICIENT AND SELECTIVE CONVERSION OF ALDEHYDES AND ACETALS TO THEIR 1,3-DITHIANE DERIVATIVES WITH 2,2-DIMETHYL-2-SILA-1,3-DITHIANE1
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Aldehydes and acetals are cleanly and rapidly converted to the corresponding dithianes with 2,2-dimethyl-2-sila-1,3-dithiane and stochiometric amounts of boron trifluoride etherate even in the presence of ketones, which do not react competitively with the reagent.
- Soderquist, John A.,Miranda, Edgar I.
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- ACTIVATION AND SYNTHETIC APPLICATIONS OF THIOSTANNANES. CONVERSION OF ALDEHYDES AND ACETALS INTO 1,3-DITHIANES WITH HIGH CHEMODIFFERENTIATION
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Novel method for transforming aldehydes and acetals into 1,3-dithianes has been achieved with the aid of organotin thioalkoxides and organotin triflates.Under these reaction conditions, various acid-sensitive groups are tolerated.Differentiation between aromatic or aliphatic aldehydes and acetals has been realized.
- Sato, Tsuneo,Yoshida, Enji,Kobayashi, Takamichi,Otera, Junzo,Nozaki, Hitosi
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p. 3971 - 3974
(2007/10/02)
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- 1,3-Dithienium- and 1,3-Dithiolenium Salts, V. Determination of the Relative Reactivity of 1,3-Dithian-2-ylium Tetrafluoroborates by Intermolecular Hydride Ion Transfer
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The 1,3-dithienium- and 1,3-dithiolenium tetrafluoroborates 4 (n=3, 2) react in good yields with the (trimethylsiloxy)alkenes 3 available from β-dicarbonyl compounds to give the 2-substituted 1,3-dicarbonyl compounds 5.Owing to the formation of the difluoroboron acid esters 8 as competition products 3 has to be employed in excess, however.Reaction of 4 (n=3) with 1,3,5-cycloheptatriene (10) leads to the 1,3-dithianes 11 and the more stable tropylium tetrafluoroborate (12).The determination of the corresponding rates of reduction allows in a simple manner the ascertainment of the relative reactivities of 4.Whereas the reactivities of the aryl-substituted representatives of 4 show a sufficient correlation corresponding to the Hammett relationship, the variations of the reactivities of the alkyl substituted salts 4 can be explained on the basis of hyperconjugative stabilization.
- Stahl, Ingfried
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p. 4857 - 4868
(2007/10/02)
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