Synthesis of functional 1,2-dithiolanes from 1,3-bis-tert-butyl thioethers

Abstract

We report the one-step synthesis of diversely substituted functional 1,2-dithiolanes by reacting readily accessible 1,3-bis-tert-butyl thioethers with bromine.

Renewable and recyclable covalent adaptable networks based on bio-derived lipoic acid

“…24 The ROP of various strained cyclic disulfides to afford linear polydisulfides is well established and versatile as exemplified by numerous reaction pathways -such as thermal 25 , radical 26,27 or anionic (via thiolate) [28][29][30][31][32][33][34] . An exemplary feature of strained cyclic disulfides is their dynamic nature that results from facile thiol-disulfide exchange [35][36][37][38] and has been exploited to reversibly depolymerise (or chemically recycle) some of the aforementioned polydisulfides 27,[29][30][31]33 or to create functional supramolecular cyclic structures 39 .…”

Disulfide-Mediated Reversible Polymerization toward Intrinsically Dynamic Smart Materials

“…The former can be realized by modulating the ring strain of 1,2-dithiolanes using a substituent effect, such as the Thorpe–Ingold effect. Some recent studies on synthesis and modification methodologies expanded the building block library of 1,2-dithiolanes. − Six-membered disulfide rings are also polymerizable, , despite the fact that their lower ring strain contributes a lower enthalpic force for the ROP when compared to five-membered 1,2-dithiolanes. The diselenium bond is an emerging type of dynamic covalent bond. − Replacing the two sulfur atoms with selenium atoms can produce diselenium-mediated materials with unique dynamic properties.…”

Asymmetric total synthesis of (+)-(2R,4′R,8′R)-α-tocopherol enabled by enzymatic desymmetrization

“…HRMS (ESI) m/z [M + Na] + calcd for C 24 H 38 O 7 Na 461.2510, found 461.2510. 14 To a solution of vinylmagnesium bromide (1.0 M in THF, 95 mL, 4.0 equiv.) was added ketone 47 (3.00 g, 23.81 mmol, 1.0 equiv.)…”