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

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F67985858%3A_____%2F97%3A27020277" target="_blank" >RIV/67985858:_____/97:27020277 - isvavai.cz</a>

Result on the web

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DOI - Digital Object Identifier

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Result language

angličtina

Original language name

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

Original language description

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%.

Czech name

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Czech description

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Type

J_x - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

CEP classification

CC - Organic chemistry

OECD FORD branch

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Project

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Continuities

Z - Vyzkumny zamer (s odkazem do CEZ)

Publication year

1997

Confidentiality

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

Name of the periodical

Journal of Fluorine Chemistry

ISSN

0022-1139

e-ISSN

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Volume of the periodical

84

Issue of the periodical within the volume

1

Country of publishing house

NL - THE KINGDOM OF THE NETHERLANDS

Number of pages

9

Pages from-to

53-61

UT code for WoS article

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EID of the result in the Scopus database

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