Chemistry of [(Perfluoroalkyl)Methyl] Oxiranes. Regioselectivity of Ring Opening with O-Nucleophiles and the Preparation of Amphiphilic Monomers.

Kód výsledku v IS VaVaI

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Výsledek na webu

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DOI - Digital Object Identifier

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Jazyk výsledku

angličtina

Název v původním jazyce

Chemistry of [(Perfluoroalkyl)Methyl] Oxiranes. Regioselectivity of Ring Opening with O-Nucleophiles and the Preparation of Amphiphilic Monomers.

Popis výsledku v původním jazyce

The reactions of oxiranes RFCH2CH(ůOů)CH2 (RFC4F9, C6F13, C8F17; 4aů4c) with a series of alkanols in the presence of a Lewis acid took place at the terminal carbon atom with complete regioselectivity. 2-Hydroxyethyl methacrylate and acrylate reacted similarly. The reaction with alkane diols was controlled to proceed with one or two molecules of the oxiranes chemoselectively. Non-regioselective, base-catalysed ring opening by methacrylic acid (83% terminal attack) was discussed on the basis of the hard and soft acids and bases (HSAB) concept. A convenient transformation of the oxiranes to the corresponding diols 13aů13c via dioxolane intermediates, and their conversion to bis-methacrylates, was accomplished with overall yields of 75%ů79%. Thiourea converted the oxiranes into the corresponding thiiranes (15aů15c). The reactions afforded products generally in yields of 82%ů98%.

Název v anglickém jazyce

Chemistry of [(Perfluoroalkyl)Methyl] Oxiranes. Regioselectivity of Ring Opening with O-Nucleophiles and the Preparation of Amphiphilic Monomers.

Popis výsledku anglicky

The reactions of oxiranes RFCH2CH(ůOů)CH2 (RFC4F9, C6F13, C8F17; 4aů4c) with a series of alkanols in the presence of a Lewis acid took place at the terminal carbon atom with complete regioselectivity. 2-Hydroxyethyl methacrylate and acrylate reacted similarly. The reaction with alkane diols was controlled to proceed with one or two molecules of the oxiranes chemoselectively. Non-regioselective, base-catalysed ring opening by methacrylic acid (83% terminal attack) was discussed on the basis of the hard and soft acids and bases (HSAB) concept. A convenient transformation of the oxiranes to the corresponding diols 13aů13c via dioxolane intermediates, and their conversion to bis-methacrylates, was accomplished with overall yields of 75%ů79%. Thiourea converted the oxiranes into the corresponding thiiranes (15aů15c). The reactions afforded products generally in yields of 82%ů98%.

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CC - Organická chemie

OECD FORD obor

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Projekt

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Návaznosti

Z - Vyzkumny zamer (s odkazem do CEZ)

Rok uplatnění

1997

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Journal of Fluorine Chemistry

ISSN

0022-1139

e-ISSN

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Svazek periodika

84

Číslo periodika v rámci svazku

1

Stát vydavatele periodika

NL - Nizozemsko

Počet stran výsledku

9

Strana od-do

53-61

Kód UT WoS článku

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EID výsledku v databázi Scopus

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