0379964 - ÚOCHB 2013 RIV DE eng J - Článek v odborném periodiku
Iakobson, George - Beier, Petr
Highly selective synthesis of (E)-alkenyl-(pentafluorosulfanyl)benzenes through Horner-Wadsworth-Emmons reaction.
Beilstein Journal of Organic Chemistry. Roč. 8, 25 Jul (2012), s. 1185-1190. ISSN 1860-5397. E-ISSN 1860-5397
Grant CEP: GA ČR GAP207/12/0072
Institucionální podpora: RVO:61388963
Klíčová slova: Horner-Wadsworth-Emmons reaction * pentafluorosulfanyl group * phosphonates * sulfurpentafluoride
Kód oboru RIV: CC - Organická chemie
Impakt faktor: 2.801, rok: 2012 ; AIS: 0.628, rok: 2012
DOI: https://doi.org/10.3762/bjoc.8.131

Diethyl 2-nitro-(pentafluorosulfanyl)benzylphosphonates, available by the vicarious nucleophilic substitution reaction of meta- and para-nitro-(pentafluorosulfanyl)benzenes and diethyl chloromethylphosphonate, undergo Horner-Wadsworth-Emmons reaction with aldehydes in the presence of potassium hydroxide in acetonitrile at ambient temperature to give (E)-2-nitro-1-alkenyl-(pentafluorosulfanyl)benzenes in good yields and high stereoselectivities. Follow-up transformations of the primary products provided (E)-1-alkenyl-(pentafluorosulfanyl)benzenes and 2-(2-arylethyl)-(pentafluorosulfanyl)anilines.
Trvalý link: http://hdl.handle.net/11104/0210805