Xanthates derived from 1,3-dithiane and its monosulfoxide; one-carbon radical equivalents

Radicals in organic synthesis. Part 1

“…The xanthate derived from 1,3-dithiane has been studied as an equivalent of the formyl radical or a simple one-carbon radical equivalent, but it is of limited value, due to its highly electron-rich character, which necessitates the use of highly activated acceptors. 223 Slightly more promising is the radical chemistry of the mono-sulfoxide of 1,3-dithiane; this adds to a variety of alkenes under standard conditions, but its utility is severely limited by the formation of multiple diastereoisomers. Currently, the most promising xanthate-based one-carbon radical equivalent is cyano(ethoxythiocarbonylthio)methyl benzoate 317.…”

Powerful CarbonCarbon Bond Forming Reactions Based on a Novel Radical Exchange Process

“…[8] Further manipulations can again exploit the rich and now well-established ionic chemistry of dithianes. The last radical addition also involves a sugar derived alkene, as well as an interesting phosphonate reagent 21, which can be elongated on one side by a radical addition, as shown, and then elaborated on the other side by a classical Wittig-Horner condensation with an aldehyde or a ketone.…”

“…[8] Heterocycles such tetrazoles, benzothiazoles and imidazoles can be readily obtained by using the corresponding xanthates. A transformation involving a benzothiazole is shown starting with xanthate 14.…”

Syntheses of 2-Formyl-, 2,3-Diformyl- and 8-Formyl-1-azaazulenes

“…It is thought that introduction of 1,3-dithian-2-yl group, being a synthetic equivalent of formyl group, would be an excellent method. [19][20][21][22][23][24][25][26][27][28] Therefore, the reaction of 2-lithio-1,3-dithine with 1-azaazulenes and successive hydrolysis was examined.…”

“…Recently, as the mild conditions, hydrolysis of 2-substituted 1,3-dithianes using CH 3 I was reported. [24][25][26] solvent with tetramethylsilane as an internal standard unless otherwise stated; J values are recorded in Hz.…”