The first example of fluoro-Meinwald rearrangement

Novel fluorinated norbornadienes were synthesized in up to 95% yield by the base-induced elimination of HNO2 from 5-fluoro-5-nitro-6-arylbicyclo[2.2.1]hept-2-enes prepared, in turn, by the Diels–Alder reaction of β-fluoro-β-nitrostyrenes with cyclopentadiene. The subsequent epoxidation initiated the Meinwald type rearrangement affording 6-aryl-bicyclo[3.1.0]hex-2-ene-6-carboxylic acid fluorides as individual (1SR,5RS,6RS)-diastereomers. The transformation is the first example of fluoro-Meinwald rearrangement to form the corresponding acyl fluorides. © 2023

Авторы
Ponomarev S.A. , Larkovich R.V. , Aldoshin A.S. , Khrustalev V.N. , Nenajdenko V.G.
Журнал
Mendeleev Communications
Издательство
Royal Society of Chemistry
Номер выпуска
2
Язык
Английский
Страницы
188-190
Статус
Опубликовано
Ссылка
Внешняя ссылка
DOI
10.1016/J.MENCOM.2023.02.012
Том
33
Год
2023
Организации
  • 1 Department of Chemistry, M. V. Lomonosov Moscow State University, Moscow, 119991, Russian Federation
  • 2 Peoples Friendship University of Russia (RUDN University), Moscow, 117198, Russian Federation
  • 3 N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, 119991, Russian Federation
Ключевые слова
acyl fluorides; bicyclo[3.1.0]hex-2-ene-6-carboxylic acids; Diels–Alder reaction; epoxidation; Meinwald rearrangement; nitrostyrene; norbornadiene; norbornene; organofluorine compounds
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