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Regioselectivity in electrophilic additions to acetylenes

✍ Scribed by Alfred Hassner; R.J. Isbister; A. Friederang


Publisher
Elsevier Science
Year
1969
Tongue
French
Weight
173 KB
Volume
10
Category
Article
ISSN
0040-4039

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The title compound 1 was produced in situ from PhSeCl and AgOSO+ (Ar= p-tolyl), and underwent electrophilic addition to acetylenes to afford adducts g. The same products were unexpectedly formed from the reaction of ArSOsH and AlBN, or from the pyrolysis of ArS(O)SO+r, in the presence of acetylenes

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## Abstract 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__ ad