21792-53-0Relevant academic research and scientific papers
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
Soderquist, John A.,Miranda, Edgar I.
, p. 6305 - 6306 (1986)
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.
ACTIVATION AND SYNTHETIC APPLICATIONS OF THIOSTANNANES. CONVERSION OF ALDEHYDES AND ACETALS INTO 1,3-DITHIANES WITH HIGH CHEMODIFFERENTIATION
Sato, Tsuneo,Yoshida, Enji,Kobayashi, Takamichi,Otera, Junzo,Nozaki, Hitosi
, p. 3971 - 3974 (2007/10/02)
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.
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
Stahl, Ingfried
, p. 4857 - 4868 (2007/10/02)
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.
