Formation of Fluorinated 1‐Oxaspiro[2.5]octa‐4,7‐dienes from Polyfluorinated Cyclohexa‐2,5‐dienones with Diazomethane and Reactions with Aryl and2‐Chloroethyl Isocyanates | Zendy

Kovtonyuk Vladimir N. | Zendy; Kobrina Ljubov S. | Zendy; Kataeva, Olga M. | Zendy; Haufe Günter | Zendy

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Formation of Fluorinated 1‐Oxaspiro[2.5]octa‐4,7‐dienes from Polyfluorinated Cyclohexa‐2,5‐dienones with Diazomethane and Reactions with Aryl and2‐Chloroethyl Isocyanates

Author(s) -

Kovtonyuk Vladimir N.,

Kobrina Ljubov S.,

Kataeva, Olga M.,

Haufe Günter

Publication year - 2005

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200400559

Subject(s) - chemistry , diazomethane , substituent , aryl , medicinal chemistry , lithium (medication) , diastereomer , lithium diisopropylamide , organic chemistry , medicine , alkyl , endocrinology , ion , deprotonation

The reactions of four polyfluorinated cyclohexa‐2,5‐dienones 1a – 1d , additionally substituted with an electron withdrawing substituent at the 4‐position, with diazomethane give mixtures of two diastereomeric fluorinated 1‐oxaspiro[2.5]octa‐4,7‐dienes 2 and 3 . Compounds 2a / 3a and 2b / 3b react with aryl and 2‐chloroethyl isocyanates in the presence of lithium chloride or sodium pentafluorophenoxide to form fluorinated dihydro‐1,3‐benzoxazol‐2(3 H )‐ones 5a – 5c as the major products. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

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