Proximally bridged calix [4] arene compounds (DESC) H2 (3),(DMSHC) H2 (4),(DMSMC) H2 (5), and (DPSC) H2 (6), in which one R2Si group (R= alkyl or aryl) bridges adjacent oxygens, were synthesized via reaction between dialkyl-or diaryldichlorosilane and the corresponding calix [4] arene. Treatment of p-tert-butylcalix [4] arene with Ph2SiCl2 at room temperature or (o-MeC6H4) 2SiCl2 at 80° C gave (ClPh2SiCl) 2Calix-H2 (7) and (o- ...