Dibenzothiepins, phthalans and phthalides from 4-heterosubstituted dibenzothiins

M Yus, F Foubelo, JV Ferrández

Index: Yus, Miguel; Foubelo, Francisco; Ferrandez, Jose V. Tetrahedron, 2003 , vol. 59, # 12 p. 2083 - 2092

Full Text: HTML

Citation Number: 17

Abstract

The lithiation of 4-heterosubstituted dibenzothiins 1 (phenoxathiin, phenothiazine and thianthrene) with lithium and a catalytic amount of 4, 4′-di-tert-butylbiphenyl (DTBB, 7.5% molar) in THF at temperatures ranging from− 90 to− 78° C gives the corresponding functionalised organolithium intermediate I, which by reaction with different electrophiles [H2O, D2O, ButCHO, PhCHO, Ph (CH2) 2CHO, Me2CO, Et2CO,(CH2) 5CO,(CH2) 7CO] at ...