TY - JOUR
T1 - A convenient solvent-specific synthesis of 4-[4-acetoxy-3-(3-methylbut-2- enyl)phenyl]butyric acid
AU - Fatope, Majekodunmi O.
AU - Okogun, Joseph I.
PY - 1982
Y1 - 1982
N2 - Three types of reaction, esterification, C-alkenylation, and O-alkenylation, have been observed between the di-anion (4) and 1-bromo-3-methylbut-2-ene (5) in different solvent systems. Our studies of the effect of the medium on the behaviour of the di-anion (4) towards electrophilic attack by the bromo-alkene (5) resulted in the synthesis of analogues (2) and (6d) of a known anti-sickling agent (3) in high yield. The regioselectivity of the alkenylation reactions is rationalised in terms of solvent polarity.
AB - Three types of reaction, esterification, C-alkenylation, and O-alkenylation, have been observed between the di-anion (4) and 1-bromo-3-methylbut-2-ene (5) in different solvent systems. Our studies of the effect of the medium on the behaviour of the di-anion (4) towards electrophilic attack by the bromo-alkene (5) resulted in the synthesis of analogues (2) and (6d) of a known anti-sickling agent (3) in high yield. The regioselectivity of the alkenylation reactions is rationalised in terms of solvent polarity.
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U2 - 10.1039/p19820001601
DO - 10.1039/p19820001601
M3 - Article
AN - SCOPUS:37049105606
SN - 1472-7781
SP - 1601
EP - 1603
JO - Journal of the Chemical Society, Perkin Transactions 1
JF - Journal of the Chemical Society, Perkin Transactions 1
ER -