1998
DOI: 10.1002/(sici)1099-0690(199802)1998:2<379::aid-ejoc379>3.0.co;2-f
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IsoquinoliniumN-Arylimides and Some Cycloadditions to Heterocumulenes

Abstract: The red isoquinolinium N‐arylimides 19−23 are azomethine imines of which the C=N bond is part of an aromatic ring. The N‐(4‐nitrophenyl)imide 22 and the N‐(2‐pyridyl)imide 23 were obtained crystalline; in solution the latter equilibrates with the hexahydrotetrazine 24 as its dimer. The N‐phenylimide 19 is not stable; an isolated solid appears to be a tetramer. Generated by deprotonation of 11−13, the N‐arylimides 19−21 undergo in situ cycloadditions to carbon disulfide, phenyl isocyanate, phenyl isothiocyanate… Show more

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Cited by 34 publications
(15 citation statements)
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“…To our knowledge, there is no previously reported X-ray structure of a dimer of the type 1-1 despite the unusual N-N bond that ties the two urazole rings together via a four-atom chain of singly-bonded N atoms (tetrazane). Furthermore, although several tetrazane compounds have been reported in the literature (Bast et al,1998;Exner et al, 2000;Krageloh et al, 1984;Tokitoh et al, 1989;Wilmarth et al,1955), we were only able to locate a single instance of structural analysis via X-ray diffraction, that of hexakis(trifluoromethyl)tetrazane, 7 (Fig. 3), reported by Krumm et al (1995).…”
Section: Structure Of Dimer 2a-2amentioning
confidence: 84%
“…To our knowledge, there is no previously reported X-ray structure of a dimer of the type 1-1 despite the unusual N-N bond that ties the two urazole rings together via a four-atom chain of singly-bonded N atoms (tetrazane). Furthermore, although several tetrazane compounds have been reported in the literature (Bast et al,1998;Exner et al, 2000;Krageloh et al, 1984;Tokitoh et al, 1989;Wilmarth et al,1955), we were only able to locate a single instance of structural analysis via X-ray diffraction, that of hexakis(trifluoromethyl)tetrazane, 7 (Fig. 3), reported by Krumm et al (1995).…”
Section: Structure Of Dimer 2a-2amentioning
confidence: 84%
“…The method involving aryl isocyanate is also expected inconvenient because an additional step is needed for synthesizing the isocyanate, which may be unstable and difficult to purify in some cases, and the most commonly used method for preparing isocyanates uses the toxic phosgene or triphosgene 20 although other methods are available. 21 In addition, adding a tertiary alcohol to isocyanate can be difficult due to steric hindrance and usually a catalyst is needed. Nonetheless, among the compounds, 7a had been synthesized by transesterification of methyl carbamate with adamantyl alcohol.…”
Section: Resultsmentioning
confidence: 99%
“…Only a few examples of this type of interesting heterocycle are known (representative examples are provided in Fig. 4) and their properties remain largely unexplored (Bast et al, 1998;Exner et al, 2000;Krageloh et al, 1984;Ostrovskii et al, 2008;Tokitoh et al, 1989). It should be noted that compound 6 (which strongly resembles target compound 5) was reported to be formed as a minor by-product (12% yield) from an unusual ionic reaction, and not through the radical combination pathway proposed here (Tokitoh et al, 1989).…”
Section: Introductionmentioning
confidence: 95%