title: Cyclization of 2-acyl- and 2-thioacylaminobenzylcyclopropanes in the gas phase and solution.
abstract: Mass spectrometry proved itself to be a powerful tool to predict the directions and yields of mono- molecular reactions of organic compounds. Electron ionization (EI) and electrospray ionization (ESI) were used to study possible transformations of N-(ortho-cyclopropylmethylphenyl)arylamides I and N-(ortho- cyclopropylmethylphenyl)arylthioamides II as well as their para-isomers III and IV in a mass spectrometer and to predict directions and yields of their acid catalyzed cyclization reactions. Several five-eight-membered heterocycles were proposed as possible products of intramolecular transformations of compounds I and II. Reactions of compounds I and II in sulfuric acid solutions were carried out and the results obtained were compared with mass spectrometric data. Surprisingly, EI of the studied compounds mimics their solution reactions better than ESI.
authors.affiliation: Moscow State University, Moscow, Russian Federation. mocehops@yandex.ru
authors.forename: Albert T
authors.initials: AT
authors.lastname: Lebedev
authors.forename: Gianluca
authors.initials: G
authors.lastname: Giorgi
authors.forename: Olga A
authors.initials: OA
authors.lastname: Maloshitskaya
authors.forename: Julia
authors.initials: J
authors.lastname: Kuchumova
authors.forename: Tatiana
authors.initials: T
authors.lastname: Samgina
authors.forename: Piotr
authors.initials: P
authors.lastname: Dem'yanov
authors.forename: Nadezhda
authors.initials: N
authors.lastname: Karakhanova
authors.forename: Sergey
authors.initials: S
authors.lastname: Mochalov
authors.forename: Alexandr
authors.initials: A
authors.lastname: Fedotov