TY - JOUR
T1 - Rearrangements of norbornenyl radicals
T2 - Further evidence as to the mechanism of borohydride reduction of organomercurials
AU - Chambers, V. M.A.
AU - Jackson, W. R.
AU - Young, G. W.
PY - 1970/1/1
Y1 - 1970/1/1
N2 - Reductions of 3-acetoxy-5-norbornen-2-yl mercuric chloride, 5-acetoxy-3-nortricyclyl mercuric chloride, and 7-anti-acetoxy-2-exo- bromonorborn-5-ene with tributyltin hydride, triphenyltin hydride, or photochemically in methanol give similar isomeric mixtures of 2-exo-acetoxynorbornene, 7-anti-acetoxynorbornene, and 3-acetoxynortricyclene, as does reduction of the mercurials with sodium borohydride in aqueous tetrahydrofuran, indicating that a radical mechanism operates in the latter reaction.
AB - Reductions of 3-acetoxy-5-norbornen-2-yl mercuric chloride, 5-acetoxy-3-nortricyclyl mercuric chloride, and 7-anti-acetoxy-2-exo- bromonorborn-5-ene with tributyltin hydride, triphenyltin hydride, or photochemically in methanol give similar isomeric mixtures of 2-exo-acetoxynorbornene, 7-anti-acetoxynorbornene, and 3-acetoxynortricyclene, as does reduction of the mercurials with sodium borohydride in aqueous tetrahydrofuran, indicating that a radical mechanism operates in the latter reaction.
UR - http://www.scopus.com/inward/record.url?scp=37049135553&partnerID=8YFLogxK
U2 - 10.1039/C29700001275
DO - 10.1039/C29700001275
M3 - Article
AN - SCOPUS:37049135553
SN - 0577-6171
SP - 1275
EP - 1276
JO - Journal of the Chemical Society D: Chemical Communications
JF - Journal of the Chemical Society D: Chemical Communications
IS - 20
ER -