Open AccessRecyclization reactions of 8,10-dibromocamphor with Grignard and organolithium compounds
Author(s) -
Ihor Verenka,
Marian V. Gorichko
Publication year - 2021
Publication title -
french-ukrainian journal of chemistry
Language(s) - English
Resource type - Journals
ISSN - 2312-3222
DOI - 10.17721/fujcv9i1p97-103
Subject(s) - organolithium compounds , chemistry , grignard reagent , alkylation , fragmentation (computing) , intramolecular force , reagent , nuclear magnetic resonance spectroscopy , molecule , stereochemistry , grignard reaction , medicinal chemistry , organic chemistry , ion , catalysis , computer science , deprotonation , operating system
Grignard reagents and organolithium compounds react with 8,10-dibromocamphor to afford substituted 1-methyl-2-methylenebicyclo[3.2.0]heptanes. Recyclization proceeds via intramolecular enolate alkylation and Grob fragmentation of the reaction intermediates. All compounds have been characterized by 1H, 13C and 19F NMR spectroscopy and their chemical composition proved by HRMS analyses. The relative spatial arrangement of substituents in the molecule of (1-methyl-2-methylenebicyclo[3.2.0]heptan-6-yl)diphenylmethanol was studied by NOESY experiments.