Diisopropyl sulfide

Stannane 6a underwent facile transmetalation in tetrahydrofuran at — 78 °C on treatment with butyllithium to afford 6b. Addition of the lithium reagent 6b to a solution of 1.1 equivalents of copper(I) bromide-dimethyl sulfide in 1 1 diisopropyl sulfide/tetrahydrofuran at — 78 °C gave the copper reagent 6c, which reacted with methyl vinyl ketone at —78 "C in the presence of boron trifluoride-diethyl ether65, producing 7 in 55% yield65. 

A more direct access to the unstable and non isolated sulfonium ylides 58a- c is the reaction of diisopropyl diazomethylphosphonate 57 with allylic sulfides, catalyzed by Cu(II), Rh(II) [39], or ruthenium porphyrins.[40] For example, the a-phosphorylated y,d-unsaturated sulfides 59-61 are obtained through the [2,3] -sigmatropic rearrangement of 58a-c. This method allows the use of a greater variety of starting allylic sulfide substrates, such as 2-vinyl tetrahydrothiophene, or propargylic sulfides (Scheme 15). 

Acetyl bromide cleaves dibenzyl sulfide, while diethyl or diisopropyl are resistant (27). 

The reaction of diisopropyl sulfide with sulfur monochloride and DABCO afforded l,2-dithiolo-3-thiones 98 and 99 (1999JOC4376). Dithiole ring formation had been assumed to be similar to that produced from tertiary diisopropyl-amines. However, in the case of diisopropyl sulfide only one isopropyl group was... 

Diphenyl-1 -pyrenylphosphine hydroperoxide determination, 679-80 peroxide value, 659, 680 Diphenyl sulfide, peroxyacid reduction, 700-1 Dipolar intermediate, ene reaction, 853 Dipole moments, dioxiranes, 1132 DIPT (diisopropyl tartrate), 395 Dipyridamole, low-density hpoprotein antioxidant, 611 Di radicals... 

Diethyl tartrate is the best tartaric acid derivative for enantioselective oxidation of thioethers. This finding was established for the asymmetric oxidation of methyl p-tolyl sulfide with cumene hydroperoxide, that is, 96% ee (DET) 87% ee (diisopropyl tartrate) 62% ee (dimethyl tartrate) [24] and 1.5% ee (bis A, V-dimethy I tart rami de, r-BuOOH as the oxidant) [17]. 

Interestingly, it is possible to employ diisopropyl sulfide in the place of dimethyl sulfide in Corey-Kim oxidations, in which case primary alcohols can be oxidized in the presence of secondary ones or vice versa, depending on reaction temperature.250... 

Interestingly, when a Corey-Kim oxidation (Me2S/NCS) is performed with diisopropyl sulfide, instead of dimethyl sulfide, primary alcohols are selectively oxidized at 0°C, while lowering the temperature to —78°C causes the selective oxidation of secondary alcohols.34... 

A classical Corey-Kim oxidation sometimes shows a certain preference for the oxidation of secondary alcohols.2 Additionally, a Corey-Kim oxidation, in which diisopropyl sulfide is employed in the place of dimethyl sulfide, presents a preference for the oxidation of primary alcohols at 0°C and secondary alcohols at -78°C.50... 

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