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Diels‐Alder Reaction of β‐Fluoro‐β‐nitrostyrenes. Synthesis of Mono‐fluorinated Six‐Membered Derivatives
Author(s) -
Larkovich Roman V.,
Ponomarev Savva A.,
Aldoshin Alexander S.,
Tabolin Andrey A.,
Ioffe Sema L.,
Nenajdenko Valentine G.
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000054
Subject(s) - chemistry , aromatization , yield (engineering) , substituent , cycloaddition , diels–alder reaction , organic chemistry , base (topology) , medicinal chemistry , catalysis , mathematical analysis , materials science , mathematics , metallurgy
The Diels‐Alder reaction of β‐fluoro‐β nitrostyrenes with some linear dienes was investigated. A number of monofluorinated [4+2]‐cycloadducts was prepared in up to 90 % yield. The kinetics of [4+2]‐cycloaddition to 2,3‐dimethyl‐1,3‐butadiene was studied in detail to reveal substituent effect and activation parameters of the reaction. It was demonstrated that base‐induced elimination of nitrous acid followed by oxidative aromatization can be used for the preparation of mono‐fluorinated biphenyls in up to 92 % isolated yield.