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- Title
Unexpected molecular mechanism of trimethylsilyl bromide elimination from 2-(trimethylsilyloxy)-3-bromo-3-methyl-isoxazolidines.
- Authors
Kącka-Zych, Agnieszka; Jasiński, Radomir
- Abstract
The molecular mechanism of elimination of the trimethylsilyl bromide (2) from 2-(trimethylsilyloxy)-3-bromo-3-methyl-isoxazolidines (1a–d) has been analyzed within the molecular electron density theory using density functional theory calculations at the M06-2X(PCM)/6-31+G(d) computational level. These elimination reactions take place via a two-step mechanism involving an intermediate. Bonding evolution theory analysis allows to set apart seven phases along the reaction path. Elimination of trimethylsilyl bromide starts with rupture of the C1–Br2 bond of 2-(trimethylsilyloxy)-3-bromo-3-methyl-isoxazolidine (1a). Thereafter, we observed the formation of the N5–C1 double bond and the last step of this elimination is associated with formation of a new Br2–Si3 bond and breaking of the Si3–O4 bond.
- Subjects
DENSITY functional theory; ELECTRON density; BROMIDES; ELIMINATION reactions; DOUBLE bonds
- Publication
Theoretical Chemistry Accounts: Theory, Computation, & Modeling, 2019, Vol 138, Issue 6, pN.PAG
- ISSN
1432-881X
- Publication type
Article
- DOI
10.1007/s00214-019-2467-5