New Sulfenyl Chloride Chemistry: Synthesis, Reactions and Mechanisms toward Carbon-Carbon Double Bonds

Abstract

This review summarizes recent publications about sulfenyl chlorides including aspects of their methods of preparation, chemistry and mechanisms with carbon-carbon double bonds and disulfides 85 2. Special attention has been paid to triphenylmethanesulfenyl chloride 2 and the thio 3 and dithio homolog 4.

Efficient Regioselective Synthesis of Novel Condensed Sulfur–Nitrogen Heterocyclic Compounds Based on Annulation Reactions of 2-Quinolinesulfenyl Halides with Alkenes and Cycloalkenes

“…Addition reactions of sulfenyl halides to alkenes are well understood [ 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 , 51 , 52 , 53 ], and it is known that the reactions of arylsulfenyl halides with styrene and its derivatives also afforded Markovnikov adducts [ 42 , 43 ].…”

“…It is worth noting that electrophilic addition of arylsulfenyl halides to linear 1-alkene afforded predominantly anti-Markovnikov products, and thiiranium cations were regarded as intermediates in these reactions [ 44 , 45 , 46 , 47 ]. Taking into account these data, we suppose that the reactions of quinolinesulfenyl chloride 2 with terminal alkenes proceeded via intermediates thiiranium cation B and nucleophilic attack of the nitrogen atom of the quinoline ring occurred at the least substituted carbon atom of thiiranium ion B leading to the formation of products 4 – 6 in an anti-Markovnikov fashion ( Scheme 10 ).…”

A Regioselective Synthesis of Novel Functionalized Organochalcogen Compounds by Chalcogenocyclofunctionalization Reactions Based on Chalcogen Halides and Natural Products

“…We suppose that heating accelerates isomerization of primarily formed anti-Markovnikov adducts A into Markovnikov products B followed by intramolecular nucleophilic substitution with the formation of (2,3-dihydro-1-benzofuran-2-yl)methyl moiety ( Scheme 5 ). It is known that electrophilic addition of sulfenyl halides to 1-alkenes leads predominantly to anti-Markovnikov products [ 73 , 74 , 75 ].…”

A Novel Family of [1,4]Thiazino[2,3,4-ij]quinolin-4-ium Derivatives: Regioselective Synthesis Based on Unsaturated Heteroatom and Heterocyclic Compounds and Antibacterial Activity

“…It is known that the electrophilic addition of sulfenyl chlorides [ 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 , 51 , 52 ] to linear 1-alkene leads predominantly to anti-Markovnikov products [ 43 , 44 , 45 , 46 ] and thiiranium cations are regarded as intermediates in these reactions [ 43 , 44 , 45 , 46 , 47 , 48 ]. In the cases of 4-pentenoic and 5-hexenoic acids, allylchloride, allylbromide and allyl cyanate, there are no heteroatoms (adjacent to the double bond) which could stabilize the intermediates, and the reactions take place via thiiranium intermediate A .…”