Unexpected molecular mechanism of trimethylsilyl bromide elimination from 2-(trimethylsilyloxy)-3-bromo-3-methyl-isoxazolidines
Authors:
- Agnieszka Kącka-Zych,
- Radomir Jasiński
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.
- Record ID
- CUTc60128f056834329a5bca1dc6d76b01d
- Publication categories
- ;
- Author
- Journal series
- Theoretical Chemistry Accounts, ISSN 1432-881X, e-ISSN 1432-2234
- Issue year
- 2019
- Vol
- 138
- No
- 6
- Pages
- [1-10]
- Article number
- 81
- Other elements of collation
- rys.; tab.; Bibliografia (na s.) - 9-10; Bibliografia (liczba pozycji) - 35; Oznaczenie streszczenia - Abstr.; Numeracja w czasopiśmie - Vol. 138, Iss. 6
- Keywords in English
- elimination, trimethyl bromide, isoxazolidines, molecular electron density theory, bonding evolution theory, electron localization function
- DOI
- DOI:10.1007/s00214-019-2467-5 Opening in a new tab
- URL
- https://link.springer.com/article/10.1007/s00214-019-2467-5 Opening in a new tab
- Related project
- Teoretyczne badania nad zastosowaniem przyjaznych środowisku technik do otrzymywania bioaktywnych nitrozwiązków - potencjalnych farmaceutyków. . Project leader at PK: , ,
- Language
- eng (en) English
- License
- Score (nominal)
- 70
- Additional fields
- Indeksowana w: Scopus
- Uniform Resource Identifier
- https://cris.pk.edu.pl/info/article/CUTc60128f056834329a5bca1dc6d76b01d/
- URN
urn:pkr-prod:CUTc60128f056834329a5bca1dc6d76b01d
* presented citation count is obtained through Internet information analysis, and it is close to the number calculated by the Publish or PerishOpening in a new tab system.