The dimerization and photochemical rearrangement of pentacyclo-[5.4.0.02,6.03,10.05,9]undecane-8-thione

Read, Colin E.; Martins, Charles Ferreira; Viljoen, A. M.

doi:10.1016/j.tetlet.2004.08.092

Cited by 6 publications

(5 citation statements)

References 10 publications

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“…Adamantanthione (1a) [18] and pentacyclo [5.4.0.02,6.03,10.05,9]undecan-8-thione (1b) [9] [19] were prepared according to known protocols. The commercial dimethyl methylphosphonate was distilled prior to the use.…”

Section: Methodsmentioning

confidence: 99%

Reactions of polycyclic thioketones with a phosphonylated carbanion

Mlostoń

Obijalska

Urbaniak

et al. 2008

Heteroatom Chemistry

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Polycyclic, nonenolizable cycloaliphatic thioketones 1a and 1b react smoothly with the lithium salt of diethyl methylphosphonate 7 in THF solution at −40°C to afford products of the carbophilic attack exclusively. Quenching of the obtained lithium thiolates with alkyl iodides yields sulfanes of type 9 or 11, respectively, in good yields. 1‐Fluoro‐2,4‐dinitrobenzene was shown to act as an arylating agent. In the case of the “cage” thioketone 1b, the carbanion of salt 7 approaches the CS bond from the exo‐side exclusively. In contrast to the parent carbonyl compounds, thioketones 1 show no tendency to undergo the conversion analogous to the Horner–Wadsworth–Emmons reaction, which would result in the formation of an olefinic product. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:182–187, 2008; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20390

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Section: Methodsmentioning

confidence: 99%

Reactions of polycyclic thioketones with a phosphonylated carbanion

Mlostoń

Obijalska

Urbaniak

et al. 2008

Heteroatom Chemistry

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“…Upon heating a mixture of 2 and 3 and tetracyanoethene or N-methylmaleimide in THF solution at 40°C nitrogen evolved, and subsequent separation of the reaction .0 3,10 .0 5,9 ]undecane-8,11-dione (6) is commercially available from Sigma-Aldrich or can be prepared following a protocol in [14]. Pentacyclo[5.4.0.0 2,6 .0 3,10 .0 5,9 ]undecane-8-one (10) [11] was obtained from 6 according to a modified 4-step protocol outlined below.…”

Section: Methodsmentioning

confidence: 99%

“…Pentacyclo[5.4.0.0 2,6 .0 3,10 .0 5,9 ]undecane-8-thione (1) was synthesized by thionation of 10 using phosphorus pentasulfide as a thionating reagent and pyridine as a solvent [5] (see also [6], where the application of Lawesson's reagent is described). To an ice cold solution of 7 (21 g, 0.096 mol) in ethanol (120 ml), a cold solution of sodium borohydride (7 g in 50 ml of EtOH) was added under stirring within 5 min.…”

Section: Methodsmentioning

confidence: 99%

“…A crude mixture of 2,5-dihydro-1,3,4thiadiazolidines 2 and 3, which had been obtained from 1 and a solution of diazomethane in Et 2 O, was used for the reactions with tetracyanoethylene and N-phenylmaleimide according to [7]. Crystals of 3', 3',4',4'-tetracyanospiro[pentacyclo[5.4.0.0 2,6 .0 3,10 .0 5,9 ]undecane-8,2'-tetrahydrothiophene] (11) and 7-methylspiro [7-aza-2-thiabicyclo[3.3.0]octane-2,8'-pentacyclo [5.4.0.0 2,6 .0 3,10 .0 5,9 ]undecane-6,8-dione (12) suitable for the crystal-structure determination were grown by slow evaporation of the solvents of solutions in methanol or hexane/CH 2 Cl 2 , respectively, at room temperature. Table 1 and Figs.…”

Section: Preparation Of Cycloadducts 11 and 12mentioning

confidence: 99%

“…Recently, successful preparations of the new and stable polycyclic thioketone 1 were published [5,6]. It has been shown that 1 reacts easily with diazomethane at low temperature to yield the corresponding 2,5-dihydro-1,3,4-thiadiazole 2 as the major product along with the regioisomeric cycloadduct 3 [7] (Scheme 1).…”

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Synthesis and Structure of Spirocyclic Tetrahydrothiophene Derivatives Bearing a “Cage” Residue.

et al. 2005

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Thiophene derivatives R 0090Synthesis and Structure of Spirocyclic Tetrahydrothiophene Derivatives Bearing a "Cage" Residue. -Compounds (VIII) and (X), which are obtained from trapping of an intermediatly formed thiocarbonyl S-methanide with compounds (VII) and (IX), are characterized by X-ray crystallography. -(ROMANSKI*, J.; MLOSTON, G.; LINDEN, A.; HEIMGARTNER, H.; Pol. J. Chem. 79 (2005) 6, 973-979; Sect. Heteroorg. Compd., Univ. Lodz, PL-90-136 Lodz, Pol.; Eng.) -C. Oppel 47-110

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Reduction of Thiocarbonyl Compounds with Lithium Diisopropylamide

Gebert

Jasiński

Mlostoń

et al. 2014

Helvetica Chimica Acta

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Treatment of 4,4-disubstituted 2-phenyl-1,3-thiazole-5(4H)-thiones with lithium diisopropylamide (LDA; LiNiPr2) in THF at -78°yielded the corresponding 1,3-thiazole-5(4H)-thioles in moderate yields. Sequential treatment with LDA and MeI under the same conditions led to the 5-methylsulfanyl derivatives. Similarly, reaction of some cycloalkanethiones as well as diaryl thioketones with LDA and MeI gave cycloalkyl methyl sulfides and diarylmethyl methyl sulfides, respectively. A reaction mechanism via H transfer from LDA to the thiocarbonyl C-atom via a six-membered transition state is proposed for this unprecedented reduction of the C¼S bond.

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The dimerization and photochemical rearrangement of pentacyclo-[5.4.0.02,6.03,10.05,9]undecane-8-thione

Cited by 6 publications

References 10 publications

Reactions of polycyclic thioketones with a phosphonylated carbanion

Reactions of polycyclic thioketones with a phosphonylated carbanion

Synthesis and Structure of Spirocyclic Tetrahydrothiophene Derivatives Bearing a “Cage” Residue.

Reduction of Thiocarbonyl Compounds with Lithium Diisopropylamide

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