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Photolytic Study of 2-Azidomethylthiophene and Its Derivatives;Pyrolytic Study of 3-Cyclohexeno[b]furylmethyl Benzoate

1. Generation of nitrenes by means of photolysis of arylmethylazides and its derivatives have been studies. Pyrolysis of 2-azidomethylthiophene¡]44a¡^ gave 2-thiophenecarboxaldehyde¡]77a¡^and (2-thienylmethylidene)-2-thienylamine¡]45a¡^, and pyrolysis of 2-azidomethylbenzo[b]thiophene¡]44b¡^gave the corresponding products. Pyrolysis of 2-azido-1-(2-thienyl)ethanone¡]52a¡^gave 2-thiophenecarboxaldehyde¡]77a¡^, 2-acetylthiophene¡]80a¡^and 2-(thiophene-2-carbonyl)amino-1-(2-thienyl)ethanone¡]83a¡^, and pyrolysis of 2-azido-1-(2-benzo[b]thienyl)ethanone¡]52b¡^gave the corresponding products.
2. Pyrolysis of 3-cyclohexeno[b]furylmethyl benzoate¡]35¡^gave cyclohexeno-4-methylenecyclobuten-3-one¡]25¡^via highly reactive carbene intermediate. At high temperature, compound 25 can continue the reaction of elimination and ring opening to give benzene¡]43¡^, fulvene¡]46¡^, 2-ethylnylcyclohex-1-ene carbaldehyde¡]44¡^ and 4,5-dimethylenecyclopent-2-enone¡]45¡^.

Identiferoai:union.ndltd.org:NSYSU/oai:NSYSU:etd-0714111-143043
Date14 July 2011
CreatorsLin, Pei-jyun
ContributorsMing-Jung Wu, Teng-yuan Dong, Chin-Hsing Chou, Cherng-Chyi Tzeng
PublisherNSYSU
Source SetsNSYSU Electronic Thesis and Dissertation Archive
LanguageCholon
Detected LanguageEnglish
Typetext
Formatapplication/pdf
Sourcehttp://etd.lib.nsysu.edu.tw/ETD-db/ETD-search/view_etd?URN=etd-0714111-143043
Rightscampus_withheld, Copyright information available at source archive

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