Halogen bonding in Wagner-Meerwein rearrangement products

Reaction of (3aRS,6SR,7aRS)-6-substituted 2-phenyl-2,3,7,7a-tetrahydro-3a,6-epoxyisoindol-1(6H)-ones (1–3) with ICl (or Br2) in CH2Cl2 yields to halogenated Wagner-Meerwein rearrangement products, 4,5- (or 4,5,6)-halo-2-phenyloctahydro-4,6-epoxycyclopenta[c]pyridin-1-ones, with moderate yields (40–43%) of 4–6. All these polyhalogenated compounds are formed exclusively in the syn diastereomeric form relatively to halogen atoms at 4 and 5 positions of molecule. In 4–6 the halogenated carbon atoms exist as the S-stereogenic centers. The Cl ⋯ Cl and Cl ⋯ I types of halogen binding were found in the structures of 5 and 6, respectively, whereas molecules of 4 are stabilized in crystal by multiple hydrogen bonding. © 2017

Авторы
Zubkov F.I. 1 , Mertsalov D.F. 1 , Zaytsev V.P. 1 , Varlamov A.V. 1 , Gurbanov A.V. 2, 3 , Dorovatovskii P.V.4 , Timofeeva T.V.5 , Khrustalev V.N. 5, 6 , Mahmudov K.T. 2, 7
Редакторы
-
Издательство
Elsevier B.V.
Номер выпуска
-
Язык
Английский
Страницы
949-952
Статус
Опубликовано
Подразделение
-
Номер
-
Том
249
Год
2018
Организации
  • 1 Organic Chemistry Department, Peoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya Str., Moscow, 117198, Russian Federation
  • 2 Centro de Química Estrutural, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais, Lisbon, 1049-001, Portugal
  • 3 Organic Chemistry Department, Baku State University, Z. Xalilov Str. 23, Baku, 1148, Azerbaijan
  • 4 National Research Center “Kurchatov Institute”, Acad. Kurchatov Sq. 1, Moscow, 123182, Russian Federation
  • 5 New Mexico Highlands University, P.O. Box 9000, Las Vegas, NM 87701, United States
  • 6 Inorganic Chemistry Department, Peoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St., Moscow, 117198, Russian Federation
  • 7 Department of Ecology and Soil Sciences, Baku State University, Z. Xalilov Str. 23, Baku, 1148, Azerbaijan
Ключевые слова
3a,6-epoxyisoindole; Halogen bonding; Halogenation; Hydrogen bonding; Wagner-Meerwein rearrangement
Дата создания
19.10.2018
Дата изменения
19.10.2018
Постоянная ссылка
https://repository.rudn.ru/ru/records/article/record/7386/