TY - JOUR
T1 - Synthesis of Perylene-3,4,9,10-tetracarboxylic Acid Derivatives Bearing Four Different Substituents at the Perylene Core
AU - Dubey, Rajeev K.
AU - Westerveld, Nick
AU - Eustace, Stephen J.
AU - Sudholter, E.J.R.
AU - Grozema, Ferdinand C.
AU - Jager, Wolter F.
PY - 2016/11/4
Y1 - 2016/11/4
N2 - Nucleophilic aromatic substitution reactions on 1,7-dibromoperylene-3,4,9,10-tetracarboxylic monoimide dibutylester, using phenol and pyrrolidine reagents, have been exploited to synthesize perylenes with four different substituents at the perylene core. The first substitution is always regiospecific at the imide-activated 7-position. A second substitution reaction does not always replace the bromine at C-1, but may replace a phenol substituent at the highly activated 7-position. Exploiting this reactivity pattern, a "mixed" 1,7-diphenoxy, 1,7-dipyrrolidinyl, and two 1-phenoxy-7-pyrrolidinyl derivatives have been synthesized.
AB - Nucleophilic aromatic substitution reactions on 1,7-dibromoperylene-3,4,9,10-tetracarboxylic monoimide dibutylester, using phenol and pyrrolidine reagents, have been exploited to synthesize perylenes with four different substituents at the perylene core. The first substitution is always regiospecific at the imide-activated 7-position. A second substitution reaction does not always replace the bromine at C-1, but may replace a phenol substituent at the highly activated 7-position. Exploiting this reactivity pattern, a "mixed" 1,7-diphenoxy, 1,7-dipyrrolidinyl, and two 1-phenoxy-7-pyrrolidinyl derivatives have been synthesized.
UR - http://www.scopus.com/inward/record.url?scp=84994578353&partnerID=8YFLogxK
U2 - 10.1021/acs.orglett.6b02887
DO - 10.1021/acs.orglett.6b02887
M3 - Article
AN - SCOPUS:84994578353
SN - 1523-7060
VL - 18
SP - 5648
EP - 5651
JO - Organic Letters
JF - Organic Letters
IS - 21
ER -