Regioselective nucleophilic 1,4-trifluoromethylation of 2-polyfluoroalkylchromones with (trifluoromethyl)trimethylsilane. Synthesis of fluorinated analogs of natural 2,2-dimethylchroman-4-ones and 2,2-dimethylchromenes / Sosnovskikh VY,Usachev BI,Sevenard DV,Roschenthaler GV // JOURNAL OF ORGANIC CHEMISTRY. - 2003. - V. 68, l. 20. - P. 7747-7754.

ISSN/EISSN:

0022-3263 / нет данных

Type:

Article

Abstract:

Reactions of 2-polyfluoroalkylchromones with (perfluoroalkyl)trimethylsilanes proceed as a 1,4-nucleophilic perfluoroalkylation to give 2,2-bis(polyfluoroalkyl)chroman-4-ones with high regioselectivity and good yields after acid hydrolysis. Oxidation of 6-methyl-2,2-bis(trifluoromethyl)chroman-4-one with a mixture of K2S2O8 and CuSO4 in aqueous acetonitrile leads to fluorinated analogues of natural lactarochromal and the corresponding acid. Reduction of substituted 2,2-bis(trifluoromethyl)chroman-4-one with sodium borohydride in methanol and subsequent dehydration of chromanols in refluxing xylene in the presence of p-toluene sulfonic acid gives 2,2-bis(trifluoromethyl)chromenes, which are fluorinated analogues of natural precocenes.

Author keywords:

ANTI-JUVENILE HORMONES; CARBONYL-COMPOUNDS; TRIFLUOROMETHYLATION REACTIONS; ALKYL MERCAPTOACETATES; CONJUGATE ADDITION; ALLYLIC ALCOHOLS; FACILE SYNTHESIS; ACID; DERIVATIVES; REAGENTS

DOI:

10.1021/jo034591y

Web of Science ID:

ISI:000185609000024

Соавторы в МНС:

Другие поля

Поле	Значение
Month	OCT 3
Publisher	AMER CHEMICAL SOC
Address	1155 16TH ST, NW, WASHINGTON, DC 20036 USA
Language	English
Keywords-Plus	ANTI-JUVENILE HORMONES; CARBONYL-COMPOUNDS; TRIFLUOROMETHYLATION REACTIONS; ALKYL MERCAPTOACETATES; CONJUGATE ADDITION; ALLYLIC ALCOHOLS; FACILE SYNTHESIS; ACID; DERIVATIVES; REAGENTS
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	vyacheslav.sosnovskikh@usu.ru
Number-of-Cited-References	66
Usage-Count-Last-180-days	1
Usage-Count-Since-2013	11
Journal-ISO	J. Org. Chem.
Doc-Delivery-Number	726PW