Preparation de la cyclobutanethione; etude de ses spectres.

Paquer, D.; Vazeux, Michel

doi:10.1016/s0040-4039(01)94787-2

Cited by 6 publications

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“…The corresponding allylic bromides can be conThe retro-ene reaction, when used under the conditions of FVT, is an efficient method for generating reactive, un-verted into sulfides 8 and 9 by reaction with 2-propene-1-thiol and n-butyllithium in ether (method [A] ation has been successfully used for the generation of cyclobutanethione [13] The specificity of the thermal decomposition of compounds 8, 9, 12, and 13 decreases when increasing the FVT temperature, as shown in the case of allyl cyclohexenyl sulfide 9, which gave upon FVT at 800°C a mixture of products resulting from competitive retro-ene reactions and, mainly, β-eliminations (Scheme 3). …”

Section: Synthesis Of Precursorsmentioning

confidence: 99%

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Flash Vacuum Thermolysis – Synthesis and Characterization of Unstabilized Cycloalkenethiones

Briard

Levillain²,

Ripoll³

et al. 1999

Eur. J. Org. Chem.

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The flash vacuum thermolysis (FVT) of cycloalkenyl allyl (or propargyl) sulfides 8, 9, 12, and 13 led, as the main thermal pathway, to the conjugated cycloalkenethiones 1, 3, and 5, resulting from a retro‐ene reaction. These reactive thioketones, thus obtained in ca. 70% yield, have been characterized in the gas phase by mass spectrometry, and at low temperature by IR, UV/Vis and NMR spectroscopy. The polymerization of 1, 3, and 5 upon warming is generally more rapid than the other attempted reactions and only the [2 + 3] dipolar cycloaddition with diazomethane led in low yield, besides polymeric materials, to isomeric 1,3‐dithiolanes 20 from cyclopentenethione 1. The obtention of the nonconjugated cycloalkenethiones 2 and 4, expected in the FVT of sulfides 10 and 11, has been confirmed only by UV/Vis spectroscopy at –196 °C, due to their rapid enethiolization. In the case of the large‐ring sulfide 14, the (E) geometry of the double bond favoured the competitive retro‐ene reaction yielding cyclododecene and propynethial; on the other hand, the FVT of the tricyclic gem‐dithiol 15, a possible precursor of cyclobutenethione (7), led to vinyl thioketene (18), obtained by thermal ring opening of 7.

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Section: Synthesis Of Precursorsmentioning

confidence: 99%

“…Ϫ H 2 ), 6.89 (dt, J ϭ 9.6 and 4.2 Hz, 1 H 3 ). 13 . was performed, due to the low volatility of products, with ethanol and aq.…”

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confidence: 99%

Flash Vacuum Thermolysis – Synthesis and Characterization of Unstabilized Cycloalkenethiones

Briard

Levillain²,

Ripoll³

et al. 1999

Eur. J. Org. Chem.

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ChemInform Abstract: PREPARATION OF CYCLOBUTANETHIONE, A SPECTRAL STUDY

Paquer¹,

Vazeux²

1978

Chemischer Informationsdienst

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Electron impact induced fragmentation of some cyclic bisthioacylals

Schauble

Saun

Spaziano

1981

Org. Mass Spectrom.

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O=&--XH, Scheme 1grounds. Again the ion peak at mlz 384 in 1 is 23 times more intense than the same peak in 2. This too can be explained on the basis of steric grounds. Thus the spectra can be related to the configuration at the spirane carbon. ExperimentalThe mass spectra were measured on a Varian MAT-311(A) mass spectrometer at 70 eV using the direct insertion technique at a source temperature of about 120°C. The molecular formulae of all the ions mentioned in the text were established by accurate mass measurement.Compounds 1 and 2 were prepared according to the procedure described2 and the structure of these compounds were established on the basis of spectral e~i d e n c e .~ m / z 384 and m / z 369 CsH,, I O=C-CH=S '3 Scheme 2We are grateful to Professor W. Rahman References and Professor M. S. Ahmad for provision of ncecessary facilities and useful discussion.

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Preparation de la cyclobutanethione; etude de ses spectres.

Cited by 6 publications

References 1 publication

Flash Vacuum Thermolysis – Synthesis and Characterization of Unstabilized Cycloalkenethiones

Flash Vacuum Thermolysis – Synthesis and Characterization of Unstabilized Cycloalkenethiones

ChemInform Abstract: PREPARATION OF CYCLOBUTANETHIONE, A SPECTRAL STUDY

Electron impact induced fragmentation of some cyclic bisthioacylals

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