TY - JOUR
T1 - A Direct Method for the Construction of Benzene Rings
AU - Hill, Richard K.
AU - Carlson, Robert M.
PY - 1965
Y1 - 1965
N2 - Reaction of 1,4-diacetoxybutadiene with dienophiles at elevated temperatures yields, in many cases, aromatic products resulting from elimination of acetic acid from the first-formed Diels-Alder adducts. This reaction provides a direct synthesis of benzene rings, especially useful in the synthesis of unsymmetrical biphenyls. Dienophiles used successfully include quinones, β-nitrostyrenes, chalcones, and acetylenes. The reaction of acetylenic dienophiles with 1-acetoxybutadiene also affords aromatic products. The adduct of 1,4-diacetoxy-butadiene and benzonorbornadiene did not aromatize below temperatures of 450°, and then only with rearrangement, to yield dibenzocycloheptatriene.
AB - Reaction of 1,4-diacetoxybutadiene with dienophiles at elevated temperatures yields, in many cases, aromatic products resulting from elimination of acetic acid from the first-formed Diels-Alder adducts. This reaction provides a direct synthesis of benzene rings, especially useful in the synthesis of unsymmetrical biphenyls. Dienophiles used successfully include quinones, β-nitrostyrenes, chalcones, and acetylenes. The reaction of acetylenic dienophiles with 1-acetoxybutadiene also affords aromatic products. The adduct of 1,4-diacetoxy-butadiene and benzonorbornadiene did not aromatize below temperatures of 450°, and then only with rearrangement, to yield dibenzocycloheptatriene.
UR - http://www.scopus.com/inward/record.url?scp=33747189606&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=33747189606&partnerID=8YFLogxK
U2 - 10.1021/jo01018a074
DO - 10.1021/jo01018a074
M3 - Article
AN - SCOPUS:33747189606
SN - 0022-3263
VL - 30
SP - 2414
EP - 2417
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 7
ER -