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

DOI: 10.1039/P19840002375

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 2375 - 2382 (1984)

Update date:2022-08-05

Topics:

Authors:

Kasturi, Tirumalai R.

Rajasekhar, Betageri

Raju, Gonibella J.

Reddy, Gowravarham Madhusudhan

Sivaramakrishnan, Ramamoorthy

et al. et al.

Read Full Text PDF DownLoad Join now for total 90,000,000 free articles

Article abstract of DOI:10.1039/P19840002375

Oxidation of bis(2-hydroxy-1-naphthyl)methane (4a) with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) has been shown to give the novel compounds, cis- and trans-dispiropyran-3',1''-naphthalene>-2(1H),2''(1''H)-dione (12a) 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 X-ray crystal structure analysis of (12a).Hydrogenation of compounds (12a) and (13a) has been shown to give the dihydroxy compound (14) via C-C 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 (12a) 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).

Full text of DOI:10.1039/P19840002375

View Article Online / Journal Homepage / Table of Contents for this issue

View Article Online

Products guided by the article

Product name:Naphthalene, 1-[(2-methoxy-1-naphthalenyl)methyl]-2-[(2-methoxy-1-naphthalenyl)oxy] -

Cas No:77003-52-2

R&D Labs maybe for 77003-52-2

Shijiazhuang Haotian Chemical Co., Ltd.

Contact:86-311-85044374

Address:293 Donggang Road
Golden Union Agrochemical Import and Export Co., Ltd.

Contact:86-755-23910527

Address:Room 1106, Tower 3A, Excellence Century Center, Futian District, Shenzhen, China
Beijing eternalchem Co,. Ltd

Contact:+86-10-59484199

Address:No.58-A1026 Liangguan Street
Shanghai Surseechem Co.,Ltd.

Contact:+86-21-61318535

Address:Building 29,No.2139 Xizha Road, Fengxian District, Shanghai
Shanghai Forever Synthesis Co.,Ltd.

Contact:021-61124658

Address:Zhoukang Road,Pudong New District,Shanghai,China

Relevant to this article

Regiospecific Incorporation of Bromine and Iodine into Phenols Using (Trimethylsilyl)phenol Derivatives

Doi:10.1021/jo00157a035
(1983)
Synthesis of 3,5-diphenyl-1H-pyrazoles

Doi:10.1081/SCC-200054225
(2005)
Doi:10.1007/BF00947302
()
Novel phenylamino acetamide derivatives as potent and selective κ opioid receptor agonists

Doi:10.1016/j.bmcl.2005.10.034
(2006)
Solvent dependent selective alkylation of a bis(sulfonamide) for the synthesis of a DNA-binding chiral polyamine

Doi:10.1016/j.tetlet.2005.02.141
(2005)
Synthesis of highly substituted indolines and indoles via intramolecular [4 + 2] cycloaddition of ynamides and conjugated enynes

Doi:10.1021/ja051180l
(2005)

Article Doi