Irradiation of dithiane-aldehyde/ketone adducts in the presence of benzophenone leads to C-C bond cleavage regenerating the carbonyl compounds. It is established that the mechanism of this reaction involves photochemically induced single electron transfer from the dithiane moiety to the excited molecule of ET-photosensitizer, accompanied by mesolytic C-C cleavage in the generated cation-radical...

We report the use of 1,3-dithiane combined with aryldiazonium cation for the immobilization of biomolecules based on electrochemical addressing.

Regioselective lithiation followed by functionalization of 2-(2,4-dihalophenyl)-1,3-dithiane derivatives with different electrophiles was achieved in good to excellent yields. When the title compound is treated with n-butyl lithium, lithiation occurs selectively at the aromatic carbon having less acidic proton despite the presence of thermodynamically more acidic 1,3-dithiane proton in the same...

The apparent activation enthalpies, DH, for externally sensitized mesolytic fragmentations in benzophenone–dithiane adducts were obtained in variable temperature photolyses and compared with DFT activation barriers calculated for b-scission in the corresponding oxygen-centered radicals. The results of these experimental and theoretical studies further support the mechanism in which deprotonatio...

1,3-Dithiane-protected enones (enone dithianes) were found to undergo an intramolecular [2+2] photocycloaddition under visible-light irradiation (λ=405 nm) in the presence of a Brønsted acid (7.5-10 mol %). Key to the success of the reaction is presumably the formation of colored thionium ions, which are intermediates of the catalytic cycle. Cyclobutanes were thus obtained in very good yields (...

Carboxylic acids and amino acids are electrochemically deprotected from their 2-(hydroxymethyl)-1,3-dithiane (Dim) esters.

A practical and efficient route to the CD spiroketal (C-16-C-28) of the spongistatins is reported. Two stereocenters are introduced from chiral building blocks with the remainder introduced by substrate-controlled transformations. The key beta-keto-1,3-dithiane intermediate is generated by a dithiol conjugate addition to an ynone and the 1,3-dithiane unit in the C-ring plays a key role in the s...

In the title compound, C(20)H(16)S(2), the pyrene ring is planar [maximum deviation 0.0144 (15) Å] and the dithiane ring adopts a chair conformation. The crystal packing is stabilized by C-H⋯π inter-actions. An intra-molecular C-H⋯S hydrogen bond generates an S(5) ring motif.

The use of Me3SiO(-)/Bu4N(+) as a general activator of organotrimethylsilanes for addition reactions has been established. The broad scope of the method offers trimethylsilanes (including acetate, allyl, propargyl, benzyl, dithiane, heteroaryl, and aryl derivatives) as bench-stable organometallics that can be readily utilized as carbanion equivalents for synthesis. Reactions are achieved at rt ...