Why do the [PhSiO1.5]8,10,12 cages self-brominate primarily in the ortho position? Modeling reveals a strong cage influence on the mechanism

Author:

Bahrami M.123,Hashemi H.123,Ma X.123,Kieffer J.123,Laine R. M.12342

Affiliation:

1. Dept. of Mater. Sci. & Eng

2. Univ. of Michigan

3. Ann Arbor, USA

4. Macromolecular Sci. & Eng.

Abstract

(PhSiO1.5)8,10,12 cages are bulky, electron withdrawing like CF3; yet self-brominate (60 °C), favoring ortho substitution: PhT8 (≈85%), PhT10 (≈75%) and PhT12 (60%).

Publisher

Royal Society of Chemistry (RSC)

Subject

Physical and Theoretical Chemistry,General Physics and Astronomy

Reference47 articles.

1. A. I. Vogel , Practical Organic Chemistry , Halogenation of Aromatic Hydrocarbons , ch. 4, in preparation

2. S. N. Ege , Organic chemistry , The chemistry of aromatic compounds, Aromatic substitution reactions , ch. 20, in preparation

3. J. D. Hepworth , M. J.Waring and D. R.Waring , Aromatic chemistry , Aromatic halogen compounds , ch. 9, in preparation

4. F. Carey , Advanced organic chemistry , Aromatic substitution , ch. 20, in preparation

5. Aromatic Substitution. Nitration and Halogenation.

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