Oxidation of bis-(2-hydroxy-1-naphthyl)methane with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone. X-Ray crystal structure of a novel product

Kasturi, T. R.; Rajasekhar, Betageri; Raju, G. J.; Sivaramakrishnan, Ramamoorthy; Ramasubbu, Narayanan; Venkatesan, Κ.

doi:10.1039/c39800001087

J. Chem. Soc., Chem. Commun.

1980

DOI: 10.1039/c39800001087

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Oxidation of bis-(2-hydroxy-1-naphthyl)methane with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone. X-Ray crystal structure of a novel product

T. R. Kasturi¹,

Betageri Rajasekhar²,

G. J. Raju³

et al.

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Cited by 4 publications

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“…We have reported that' oxidation of the oxydiphenol(1) with tetrachloro-o-benzoquinone (o-chloranil) gives a mixture of two isomeric spiro products (2) and (3). Compound 3results from normal oxidative coupling, whereas (2) results from an unusual rearrangement.…”

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Oxidation of bis(2-hydroxy-1-naphthyl)methane and similar bisnaphthols with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone. Structure and synthesis of novel products

Kasturi¹,

Rajasekhar²,

Raju³

et al. 1984

J. Chem. Soc., Perkin Trans. 1

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Oxidation of bis(2-hydroxy-1-naphthyl)methane (4a) with 2,3-dichloro-5,6-dicyano-l,4-benzoquinone (DDQ) has been shown to give the novel compounds, cis-and trans-dispiro(naphtha1ene-1,2'(1'H)-naphtho[2,1-b)pyran-3',1 "-naphthalene}-2(1 H),2"(1 "H)-dione (1 2a) and (13a) together with the quinone methide dimer (6a) and the spiroketone (5a). Compounds (12a) and (13a) were characterised on the basis of their spectral properties and the structures were finally confirmed by an Xray crystal structure analysis of (1 2a). Hydrogenation of compounds (I 2a) and (1 3a) has been shown t o give the dihydroxy compound (14) via CC bond cleavage. An alternative synthesis of the dispironaphthalenones (12a) and (13a) was achieved by oxidation of the dihydroxy compound (14), prepared by an independent method. The generality of the oxidation of bisnaphthols of type (4a) to give novel products of the type (1 2a) and (13a) has been shown by studying the oxidation of the variously substituted bisnaphthols (4b-d,f) with DDQ. A mechanism has been proposed invoking the intermediacy of the quinol ethers (22) and (24).

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confidence: 99%

Oxidation of bis(2-hydroxy-1-naphthyl)methane and similar bisnaphthols with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone. Structure and synthesis of novel products

Kasturi¹,

Rajasekhar²,

Raju³

et al. 1984

J. Chem. Soc., Perkin Trans. 1

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ChemInform Abstract: OXIDATION OF BIS(2‐HYDROXY‐1‐NAPHTHYL)METHANE WITH 2,3‐DICHLORO‐5,6‐DICYANO‐1,4‐BENZOQUINONE. X‐RAY CRYSTAL STRUCTURE OF A NOVEL PRODUCT

Kasturi¹,

Rajasekhar²,

Raju³

et al. 1981

Chemischer Informationsdienst

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Oxidation of spiroketones with DDQ - synthesis of tropone derivatives and DDHQ diesters

et al. 1992

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Oxidation of bis-(2-hydroxy-1-naphthyl)methane with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone. X-Ray crystal structure of a novel product

Cited by 4 publications

References 0 publications

Oxidation of bis(2-hydroxy-1-naphthyl)methane and similar bisnaphthols with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone. Structure and synthesis of novel products

Oxidation of bis(2-hydroxy-1-naphthyl)methane and similar bisnaphthols with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone. Structure and synthesis of novel products

ChemInform Abstract: OXIDATION OF BIS(2‐HYDROXY‐1‐NAPHTHYL)METHANE WITH 2,3‐DICHLORO‐5,6‐DICYANO‐1,4‐BENZOQUINONE. X‐RAY CRYSTAL STRUCTURE OF A NOVEL PRODUCT

Oxidation of spiroketones with DDQ - synthesis of tropone derivatives and DDHQ diesters

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