- Preparation, 13C NMR/DFT/IGLO study of benzylic mono- and dications, and attempted preparation of a trication
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Substituted benzylic mono- and dications were prepared and investigated by 1H and 13C NMR spectroscopy and DFT/IGLO calculations. Combined experimental and theoretical study suggest that the structure 1a is the major resonance contributor to the 2,4,6-trimethylbenzyl cation 1. Similar results were also found for the 2,4,6-dimethyl-4-tert-butylbenzyl 2 and 2,3,4,5,6- pentamethylbenzyl cation 3. It was found that the structure 4a is the predominant resonance contributor to the overall structure of 2,6- dimethylmesityldiyl dication 4 wherein the dienyl and allylic cation units are insulated from each other. Similar studies indicate structure 5a as the predominant canonical structure for 5-methoxy-2,6-dimethyl-m-xylyldiyl dication 5 wherein the dienyl and oxoallylic cation units are insulated from each other. Attempts to generate the 2,3,5,6-tetramethyl-1,4- dimethylbenzenediyl dication 8 was, however, not successful as were the generation of the 2,4,6-trimethylmesityltriyl trication 10 by ionization of 2,4,6-bis(chloromethyl)-mesitylene. The resulting ion was characterized as a chloromethyl substituted dication 9.
- Olah, George A.,Shamma, Tatyana,Burrichter, Arwed,Rasul, Golam,Prakash, G. K. Surya
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- A SIMPLE AND INEXPENSIVE PROCEDURE FOR CHLOROMETHYLATION OF CERTAIN AROMATIC COMPOUNDS
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Reaction of a range of aromatic compounds with methoxyacetyl chloride and aluminium chloride in either nitromethane or carbon disulphide results in chloromethylation in good to excellent yield.
- McKillop, Alexander,Madjdabadi, Fereidon Abbasi,Long, David A.
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p. 1933 - 1936
(2007/10/02)
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