TY - JOUR
T1 - The synthesis of barbaralyl systems via bicyclic[3.2.2] irontricarbonyl cations
AU - Abramson, S.
AU - Eisenstadt, A.
PY - 1980
Y1 - 1980
N2 - Reaction of bicyclo[3.2.2] tertiary alcohols 7b,c and 23b with Fe2(CO)9, resulted in the corresponding dienyl Fe(CO)3 complexes, which upon HBF4/Ac2O treatment yielded the bicyclo [3.2.2] dienyl irontricarbonyl cations. Nucleophilic addition of CN- to those cations, resulted in the formation of δ,μ-bonded complexes, which were degraded with Me3NO to give substituted tricydic hydrocarbons (barbaralyl systems) in unusual positions. For purpose of comparison, the trifluoroacetolysis of 2-methyl-endo-6,7-benzobicyclo[3.2.2] nonatriene (22) has been studied.
AB - Reaction of bicyclo[3.2.2] tertiary alcohols 7b,c and 23b with Fe2(CO)9, resulted in the corresponding dienyl Fe(CO)3 complexes, which upon HBF4/Ac2O treatment yielded the bicyclo [3.2.2] dienyl irontricarbonyl cations. Nucleophilic addition of CN- to those cations, resulted in the formation of δ,μ-bonded complexes, which were degraded with Me3NO to give substituted tricydic hydrocarbons (barbaralyl systems) in unusual positions. For purpose of comparison, the trifluoroacetolysis of 2-methyl-endo-6,7-benzobicyclo[3.2.2] nonatriene (22) has been studied.
UR - http://www.scopus.com/inward/record.url?scp=33748830359&partnerID=8YFLogxK
U2 - 10.1016/0040-4020(80)85032-0
DO - 10.1016/0040-4020(80)85032-0
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AN - SCOPUS:33748830359
SN - 0040-4020
VL - 36
SP - 105
EP - 115
JO - Tetrahedron
JF - Tetrahedron
IS - 1
ER -