Back to Search
Start Over
Regioselective Oxazolination of … and Formation of cis-1 C70 Adduct with Respect to the Apical Pentagon.
- Source :
-
Journal of Organic Chemistry . 9/7/2012, Vol. 77 Issue 17, p7299-7306. 8p. - Publication Year :
- 2012
-
Abstract
- Oxazolination of C70 has been achieved via the aerobic oxidation of Due to image rights restrictions, multiple line equation(s) cannot be graphically displayed. in the presence of PhCN. Only one C70 oxazoline regioisomer (1) is obtained, indicating that the oxazolination of Due to image rights restrictions, multiple line equation(s) cannot be graphically displayed. occurs with an unusual regioselectivity. Further benzylation of 12- with benzyl bromide leads to the formation of the first cis-1 C70 derivative with respect to the apical pentagon (2), as shown by the X-ray single-crystal structure and various spectral characterizations. The structure of the obtained C70 oxazoline (1) is resolved with H/D labeling benzylation and HMBC (heteronuclear multiple bond coherence) NMR on the basis of the structure of 2. The result shows that for compound 1, the O atom is selectively bonded to the C1, while the N atom is bonded to the C2 of C70. The exhibited regioselectivity for the orientation of oxazolino group on C70 is further rationalized with computational calculations, and a reaction mechanism for the oxazolination of Due to image rights restrictions, multiple line equation(s) cannot be graphically displayed. is proposed. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00223263
- Volume :
- 77
- Issue :
- 17
- Database :
- Academic Search Index
- Journal :
- Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 82117407
- Full Text :
- https://doi.org/10.1021/jo301017a