Gas-phase cyclisation reactions of 1-(2-arylthiophenyl)alkaniminyl and 2-(aryliminomethyl)thiophenoxyl radicals

Creed, Tim; Leardini, Rino; McNab, Hamish; Nanni, Daniele; Nicolson, Iain S.; Reed, David

doi:10.1039/b009844m

Cited by 26 publications

(9 citation statements)

References 22 publications

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“…The solvent then evaporated under vacuum. o ‐mercaptoacetophenone and o ‐mercaptobenzophenone were prepared according to previously described procedures. Physical constants are given in Table .…”

Section: Methodsmentioning

confidence: 99%

NMR, MP2, and DFT study of thiophenoxyketenimines (o‐thio‐Schiff bases): Determination of the preferred form

Saeed

Elias

Kamounah

et al. 2017

Magnetic Reson in Chemistry

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Five new thiophenoxyketinimines have been synthesized. H and C NMR spectra as well as deuterium isotope effects on C chemical shifts are determined, and spectra are assigned. DFT and MP2 calculations of both structures, chemical shifts, and isotope effects on chemical shifts are done. The combined analysis reveals that the compounds are primarily on a zwitterionic form with an NH and a S group and with a little of the neutral form mixed in. Very strong intramolecular hydrogen bonding is found and very high NH chemical shifts are observed. The theoretical calculations show that calculations at the MP2 level are best to obtain correct "C═S" chemical shifts.

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Section: Methodsmentioning

confidence: 99%

NMR, MP2, and DFT study of thiophenoxyketenimines (o‐thio‐Schiff bases): Determination of the preferred form

Saeed

Elias

Kamounah

et al. 2017

Magnetic Reson in Chemistry

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“…160 FVP (flash vacuum pyrolysis) of oxime-ethers yields 1,3-benzoxazines 161 and benz [d]isothiazoles and benzothiophenes from oxime sulfides. 162 Thermal decomposition of tert-butyl o-(phenylsulfanyl)-and o-(phenylsulfonyl)phenyliminoxyperacetates yields benzoisothiazoles and phenanthridines. 163 Treatment of N-azinylpyridinium N-aminides with (TMS) 3 SiH gave pyrazolopyridines.…”

Section: Heteroarenesmentioning

confidence: 99%

Synthesis of heterocycles by radical cyclisation

Bowman

Fletcher

Potts

2002

J. Chem. Soc., Perkin Trans. 1

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“…We have also shown that thiophenoxyl radicals, once formed, can in appropriate circumstances cyclise efficiently to benzothiophenes, though realistically a much better route to 2-benzylthiobenzaldehyde 12 (or its S-allyl analogue) will be required before the route is synthetically viable. We have therefore addressed this problem 15 and application of the nucleophilic substitution method 15 to benzothiophene precursors, and their subsequent cyclisation reactions, will be reported in a later paper. …”

Section: Methodsmentioning

confidence: 99%

Approaches to benzo[b]thiophenes by gas-phase pyrolysis of methyl 2-(alkylthio)cinnamates

Brown¹,

Cadogan²,

MacPherson³

et al. 2006

Arkivoc

Self Cite

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Flash vacuum pyrolysis (FVP) of 3-[2-(t-butylthio)phenyl]propenoate 7 at 700 °C (0.01 Torr) unexpectedly gave a mixture of benzo[b]thiophene derivatives 5 (15%) and 8 (21%), and thiocoumarin 9 (28%). Control experiments show that thiophenoxyls (e.g. 15) cyclise efficiently to benzo [b]thiophene 5 under similar conditions. It follows that FVP of S-t-butyl derivatives of thiophenols, is not an efficient means of generating thiophenoxyl radicals owing to competing hydrogen capture processes.

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Gas-phase cyclisation reactions of 1-(2-arylthiophenyl)alkaniminyl and 2-(aryliminomethyl)thiophenoxyl radicals

Cited by 26 publications

References 22 publications

NMR, MP2, and DFT study of thiophenoxyketenimines (o‐thio‐Schiff bases): Determination of the preferred form

NMR, MP2, and DFT study of thiophenoxyketenimines (o‐thio‐Schiff bases): Determination of the preferred form

Synthesis of heterocycles by radical cyclisation

Approaches to benzo[b]thiophenes by gas-phase pyrolysis of methyl 2-(alkylthio)cinnamates

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