ISSN:
0947-3440
Schlagwort(e):
Electrophilic addition
;
Tetradehydrodianthracene
;
Solvent effects
;
Chemistry
;
Organic Chemistry
Quelle:
Wiley InterScience Backfile Collection 1832-2000
Thema:
Chemie und Pharmazie
Notizen:
5,12:6,11-Di[1,2]benzenodibenzo[a,e]cyclooctene (tetrade-hydrodianthracene, TDDA) (1) reacts with halogens to give transannular (anti) 4, 5 and ring-opened (syn) products 6, 7. The product ratio shows a remarkable solvent dependence. Solvents of medium polarity favor anti addition, whereas syn addition is observed both with increasing and decreasing polarity. For instance, chlorine in toluene adds 100% syn, in dichloroethane 56 % anti, and in trifluorethanol again 100% syn. It is concluded that, depending on solvent polarity, three different mechanisms for electrophilic addition are operative.
Zusätzliches Material:
1 Ill.
Materialart:
Digitale Medien
URL:
http://dx.doi.org/10.1002/jlac.1995199507170
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