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The Reaction of Norbornene with Lead Tetraacetate and Thallium Trinitrate. Preliminary communication
Author(s) -
Kagan Jacques
Publication year - 1972
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19720550709
Subject(s) - chemistry , norbornene , carbocation , methanol , acetic acid , thallium , yield (engineering) , medicinal chemistry , benzene , organic chemistry , 2 norbornyl cation , materials science , monomer , metallurgy , polymer
The reaction of norbornene with lead tetraacetate is found to be much more complex than previously reported. In acetic acid and in benzene, the syn ‐7‐norbornenyl, 3‐nortricyclyl, and syn and anti ‐7‐acetoxy‐ exo ‐2‐norbornyl acetates were characterized. In methanol, the isolated products represented most of those expected from the competition of methanol and acetate in the neutralization of the intermediate carbocations. The reaction of norbornene with thallium trinitrate in the above solvents yielded very complex mixtures besides the above mentioned products which were formed in about 50% yield.