Notiz über die Darstellung von Vinylenthioncarbonat und einigen alkyl‐ sowie arylsubstituierten Derivaten

Fischler, H.-M.; Hartmann, Willy

doi:10.1002/cber.19721050838

Cited by 10 publications

(1 citation statement)

References 6 publications

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“…Isopropylphosphonothioic Dichloride. To a slurry of anhydrous aluminum chloride (53.2 g, 0.4 mol) and phosphorus trichloride (27.4 g, 0.2 mol) in dichloromethane (200 mL) was introduced dropwise isopropyl chloride (15.7 g, 0.2 mol) at [20][21][22][23][24][25] °C. After completion of the addition, the solution was stirred for 0.5 h more.…”

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Photolysis of vinylene thioxocarbonates: a new source of ketocarbenes

Torres¹,

Clement²,

Strausz³

1980

J. Org. Chem.

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confidence: 99%

Photolysis of vinylene thioxocarbonates: a new source of ketocarbenes

Torres¹,

Clement²,

Strausz³

1980

J. Org. Chem.

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Olefin Synthesis by Deoxygenation of Vicinal Diols

Block

1984

Organic Reactions

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Since the discovery in 1963 that 1,3‐dioxolane‐2‐thiones (cyclic thionocarbonates) undergo stereospecific fragmentation to olefins on heating with trivalent phosphorus compounds (the Corey–Winter reaction), a variety of approaches have been developed for the regio‐ and stereospecific (or stereo‐selective) deoxygenation of vicinal diols based on syn elimination from cyclic derivatives. These methods have been particularly useful in synthesizing substrates with delicate structural features such as strained and twisted olefins, unsaturated carbohydrates, macrocyclic lactones, lipids, and polyenes, as well as in establishing the stereochemistry of diol functions in natural products. This chapter deals primarily with deoxygenation of vicinal diols via cyclic species with X = C, P, Ti, W, or S (suitably functionalized). Brief coverage is given to deoxygenation processes that do not involve cyclic intermediates, whereas routes proceeding via oxiranes or vic ‐dihalides as separately isolated intermediates are excluded from consideration. The stereochemical equilibration of vicinal diols and the conversion of vicinal hydroxy thiols and dithiols to olefins are also covered in this chapter. Brief reviews have appeared in the literature of the Corey–Winter reaction and of the general topic of deoxygenation of vicinal diols.

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Dikation‐ether und verwandte Verbindungen, 1. Über Dikation‐chalkogenide und ‐dichalkogenide

Maas

Singer

1983

Chem. Ber.

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N,N-, N,S-, S,Sund 0,O-substituierte Thione 4 a -f und Selone 6a-c reagieren rnit Trifluormethansulfonslureanhydrid zu Dikation-disulfiden 5 af bzw. -diseleniden 7ac. Die Bildung von Dikation-sulfiden (Dikation-seleniden), welche eine Parallele zum Reaktionsverhalten der analogen Harnstoffderivate darstellen wiirde, wird nicht beobachtet. Diese Verbindungsklasse (14, 15) ist jedoch durch Reaktion von Dikation-ethern 13 rnit Thionen 4 bzw. Selonen 6 zuglnglich. 'H-und 13C-NMR-Daten der Dikation-dichalkogenide und -chalkogenide werden miteinander verglichen. Dication Ethers and Related Compounds, 1 On Dication Chalkogenides and DichalkogenidesReaction of N,N-, N,S-, S,S-, and 0,O-substituted thiones 4a-f or selones 6 a -c with trifluoromethanesulfonic anhydride leads to dication disulfides 5 af or diselenides 7a-c, resp. No dication sulfides or selenides are obtained whose formation would parallel the reactivity of the corresponding urea derivatives. This class of dications (14, 15) is, on the other hand, accessible by the reaction of dication ethers 13 with thiones 4 or selones 6. 'H and 13C NMR data of the dication dichalkogenides and chalkogenides are compared with each other.Mit der Umsetzung von TrifluormethansulfonsBureanhydrid (Tf20) rnit ,,aktivierten" Carbonylverbindungen wurde kiirzlich ein variatonsflhiger Syntheseweg zu Dikation-ethern 1 gefunden, einer Substanzklasse, die zuvor rnit wenigen Ausnahmen l s 2 ) nicht bekannt war. Die Reaktion verlluft iiber bisweilen faRbare Trifloxysalze und scheint immer dann zu gelingen, wenn die positive Ladung im Fragment R,C+ wirksam stabilisiert werden kann. (4n + 2)x-Annulenone, Harnstoffe, Pyrone etc. bieten sich somit fur diese Reaktion an3). OTfe 2 OTfOAuf Thiocarbonylverbindungen lieB sich dieser Reaktionstyp jedoch nicht iibertragen. Statt zu Dikation-thioethern 2 reagieren Thioharnstoffe rnit Trifluormethansulfonslureanhydrid unter oxidativer Dimerisierung zu Bis(formamidinium)-disulfiden (3, R = NR'J 4).

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Notiz über die Darstellung von Vinylenthioncarbonat und einigen alkyl‐ sowie arylsubstituierten Derivaten

Cited by 10 publications

References 6 publications

Photolysis of vinylene thioxocarbonates: a new source of ketocarbenes

Photolysis of vinylene thioxocarbonates: a new source of ketocarbenes

Olefin Synthesis by Deoxygenation of Vicinal Diols

Dikation‐ether und verwandte Verbindungen, 1. Über Dikation‐chalkogenide und ‐dichalkogenide

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