Pretvorbe α-oksoketen ditioacetalov v prisotnosti joda

Vrabec, Meta (author), Jereb, Marjan (mentor)

V magistrski nalogi sem raziskovala pretvorbo α-oksoketen ditioacetalov v prisotnosti joda s perfluorofenil hidrazinom. Pri tem so nastali 5-(metilsulfanil)-1-(pentafluorofenil)-1H-pirazoli. V nalogi je opisana in komentirana priprava izhodnih spojin. Naslovne pretvorbe so potekale v aprotičnih topilih in s 40–60 mol% joda kot promotorja. Izkoristki reakcij so v večini primerov zmerno dobri. Med izkoristki in stereoelektronskimi efekti substituentov ni jasne povezave. Vse nove produkte sem karakterizirala z 1H, 13C in 19F NMR, IR spektroskopijo, elementno analizo in/ali masno spektroskopijo visoke ločljivosti in izmerila njihovo tališča.

• Language: Slovenian
• Keywords: α-oksoketen ditioacetali, jod, pentafluorofenil hidrazin, 5-(metilsulfanil)-1-(pentafluorofenil)-1H-pirazoli
• Work type: Master's thesis/paper
• Typology: 2.09 - Master's Thesis
• Organization: FKKT - Faculty of Chemistry and Chemical Technology
• Year: 2021
• PID: 20.500.12556/RUL-131634
• COBISS.SI-ID: 87701507
• Publication date in RUL: 30.09.2021

Secondary language

• Language: English
• Title: Transformations of α-oxoketene dithioacetals in the presece of iodine

Abstract

In this master thesis the investigation of transformation of α-oxoketene dithioacetals in the presence of iodine with pentafluorophenyl hydrazine is presented. It resulted in formation of 5-(methylsulfanyl)-1-(pentafluorophenyl)-1H-pyrazoles. Synthesis of α-oxoketene dithioacetals is also reported and discussed. Their transformation occured in aprotic solvents and with 40–60 mol% of iodine as promotor. Most reactions gave good yields. There is no clear correlation between the yield and stereoelectronic effects of the substituents. All new substances were characterised by 1H-, 13C- and 19F-NMR, IR spectroscopy, elemental analysis and/or mass spectrometry and by measuring their melting point.

• Keywords: α-oxoketene dithioacetals, iodine, pentafluorophenyl hydrazine, 5-(methylsulfanyl)-1-(pentafluorophenyl)-1H-pyrazoles