Synthese von<i>N</i>-Arylthio-2-imino-1,3-dithiolen durch Reaktion von 2-Arylthio-1,3-dithiolium-Salzen mit Natriumazid

Fanghänel, E.; Kühnemund, K.‐H.; Richter, A. M.

doi:10.1055/s-1983-30219

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“…Arylation of 1,3-dithiol-2-thiones 278 with aryl diazonium led to 1,3-dithiolium salts 279, which react with sodium azide to give the N-arylthio-2-imino-1,3-dithiols 280 (Scheme 112). 131 1,3-Dithiolium carbenes, generated from 2-methoxy-1,3dithiols 281, were inserted into the N-H bond of N-methylbenzamide, acetanilide and succinamide to form N-(1,3dithiol-2-yl) amides and imides 282, respectively (Scheme 113). 132,133 Hydrolysis of ester 283 with a mixture of concentrated acetic acid and hydrochloric acid gave 78% of compound 284 after 28 hours (Scheme 114).…”

Section: Scheme 111mentioning

confidence: 99%

Synthesis and Chemistry of Dithiols

Elgemeie¹,

Sayed²

2001

Synthesis

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Section: Scheme 111mentioning

confidence: 99%

Synthesis and Chemistry of Dithiols

Elgemeie¹,

Sayed²

2001

Synthesis

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α-Thioxothioamides: A Formal [4+1] Cycloaddition Reaction with Isocyanides and Diisocyanides and its Application to a New Straightforward Formation of Extended Tetrathiafulvalenes

Morel¹,

Marchand²,

Sinbandhit³

et al. 2001

Eur. J. Org. Chem.

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A number of 2‐(alkylimino) and 2‐(arylimino)‐1,3‐dithioles (aza DTFs) bearing push‐pull substituents have been prepared under mild conditions according to the title procedure. This novel strategy relies upon the fact that the use of conjugated diisocyanides allows an effective synthesis of new extended tetrathiafulvalenes (TTFs). The two dithiole moieties are linked by a conjugated framework that incorporates a phenyl, biphenyl or azobiphenyl group. High and low temperature measurements are required in order to understand the complex 1H and 13C NMR spectra of the prepared mono‐, bis‐ and tris‐(1,3‐dithiole) derivatives. Their electrochemical oxidations are also described.

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Nucleophilic Aromatic Substitutions of Hydrogen

Terrier

2013

Modern Nucleophilic Aromatic Substitution

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Synthese vonN-Arylthio-2-imino-1,3-dithiolen durch Reaktion von 2-Arylthio-1,3-dithiolium-Salzen mit Natriumazid

Cited by 7 publications

References 0 publications

Synthesis and Chemistry of Dithiols

Synthesis and Chemistry of Dithiols

α-Thioxothioamides: A Formal [4+1] Cycloaddition Reaction with Isocyanides and Diisocyanides and its Application to a New Straightforward Formation of Extended Tetrathiafulvalenes

Nucleophilic Aromatic Substitutions of Hydrogen

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