TY - JOUR
T1 - Organic synthesis with α-chloro sulphides. Preparation of aromatic γ-lactones from phenols and α-chloro sulphide carboxylates
AU - Kennedy, Michael
AU - McKervey, M. Anthony
AU - Maguire, Anita R.
AU - Naughton, Sean
PY - 1990
Y1 - 1990
N2 - Lewis acid-catalysed alkylation of para-substituted phenols using α-chloro sulphides as electrophiles yields sulphenylated γ-lactones which can be desulphurised with zinc in acetic acid or Raney nickel. This synthesis has been applied to p-cresol, 2-naphthol, and two phenolic dihydrocinnamates. Alkylation of 1,4-dimethoxybenzene yields homogentisic acid dimethyl ether after desulphurisation and hydrolysis.
AB - Lewis acid-catalysed alkylation of para-substituted phenols using α-chloro sulphides as electrophiles yields sulphenylated γ-lactones which can be desulphurised with zinc in acetic acid or Raney nickel. This synthesis has been applied to p-cresol, 2-naphthol, and two phenolic dihydrocinnamates. Alkylation of 1,4-dimethoxybenzene yields homogentisic acid dimethyl ether after desulphurisation and hydrolysis.
UR - https://www.scopus.com/pages/publications/37049068361
U2 - 10.1039/p19900001041
DO - 10.1039/p19900001041
M3 - Article
AN - SCOPUS:37049068361
SN - 1472-7781
SP - 1041
EP - 1045
JO - Journal of the Chemical Society, Perkin Transactions 1
JF - Journal of the Chemical Society, Perkin Transactions 1
IS - 4
ER -