1-bromo-4-(trimethoxymethyl)benzene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Using a method analogous to that described in stage iv of Example 5 2,2-di-hydroxymethyl-pentan-1-thiol and trimethyl 4-bromo-orthobenzoate were reacted together to give 1-(4-bromophenyl)-4-n-propyl-2,6-dioxa-7-thiabicyclo[2,2,2]octane (colourless solid). were reacted together

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Trimethyl 4-bromo-orthobenzoate (1.5 g.) (McElvain and Venerable, J. Amer. Chem. Soc., 1950, 72, 1661) was added to 2-(2,2-dimethylpropyl)-2-hydroxymethyl-propan-1,3-diol (1.0 g.). One drop of concentrated hydrochloric acid was added and the mixture was maintained at 140° for one hour, under a current of nitrogen. The volatile components were removed in vacuo (1.0 mm), at 140° C. the mixture was maintained at 140° for one hour The volatile components were removed in vacuo (1.0 mm), at 140° C.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Using a method analogous to that described in stage iv of Example 5 2,2-di-hydroxymethyl-pentan-1-thiol and trimethyl 4-bromo-orthobenzoate were reacted together to give 1-(4-bromophenyl)-4-n-propyl-2,6-dioxa-7-thiabicyclo[2,2,2]octane (colourless solid). were reacted together

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Trimethyl 4-bromo-orthobenzoate (1.5 g.) (McElvain and Venerable, J. Amer.Chem.Soc., 1950,72,1661) was added to 2-(2,2-dimethylpropyl)-2-hydroxymethyl-propan-1,3-diol (1.0 g.). One drop of concentrated hydrochloric acid was added and the mixture was maintained at 140° for one hour, under a current of nitrogen. The volatile components were removed in vacuo (1.0 mm), at 140° C. the mixture was maintained at 140° for one hour The volatile components were removed in vacuo (1.0 mm), at 140° C.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-(4-Bromophenyl)-4-n-propyl-2-oxa-6,7-dithiabicyclo[2,2,2]octane was prepared from trimethyl 4-bromo-orthobenzoate and 2-hydroxymethyl-2-n-propyl-propan-1,3-dithiol.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-(4-Bromophenyl)-4-n-propyl-2-oxa-6,7-dithiabicyclo[2,2,2]octane was prepared from trimethyl 4-bromo-orthobenzoate and 2-hydroxymethyl-2-n-propyl-propan-1,3-dithiol.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: From 2,2-di-hydroxymethyl-3,3-dimethyl-butan-1-thiol and trimethyl 4-bromo-orthobenzoate, trimethyl 4-chloro-orthobenzoate, trimethyl orthocyclohexylcarboxylate and trimethyl ortho-cycloheptylcarboxylate in the manner described previously, the following compounds were prepared: the following compounds were prepared

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: From 2,2-di-hydroxymethyl-3,3-dimethyl-butan-1-thiol and trimethyl 4-bromo-orthobenzoate, trimethyl 4-chloro-orthobenzoate, trimethyl orthocyclohexylcarboxylate and trimethyl ortho-cycloheptylcarboxylate in the manner described previously, the following compounds were prepared: the following compounds were prepared

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In an analogous manner, from 2,2-di-hydroxymethyl-3-methyl-butan-1-thiol or 2,2-di-hydroxymethyl-3-methyl-pentan-1-thiol and trimethyl 4-bromoorthobenzoate or trimethyl 4-chloro-orthobenzoate or trimethyl orthocyclohexyl-carboxylate the following compounds were prepared:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (iv)b) Using a method analogous to that described in (iv)(a) above 2,2-di-(hydroxymethyl)-pentan-1-thiol and trimethyl 4-bromo-orthobenzoate were reacted together to give 1-(4-bromophenyl)-4-n-propyl-2,6-dioxa-7-thiabicyclo[2,2,2]octane. were reacted together

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (iv)b) Using a method analogous to that described in (iv)(a) above 2,2-di-(hydroxymethyl)-pentan-1-thiol and trimethyl 4-bromo-orthobenzoate were reacted together to give 1-(4-bromophenyl)-4-n-propyl-2,6-dioxa-7-thiabicyclo[2,2,2]octane. were reacted together

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (iv)a) 2,2-Di-(hydroxymethyl)-butanethiol (0.5 g.), trimethyl 4-bromo-orthobenzoate 2 (1.0 g.) and triethylamine (0.1 ml.) were heated at 130°, under a current of nitrogen, for 45 minutes. The volatile components were removed in vacuo (2.00 mm.), at 140°. The residue was purified by chromatography on alumina (alumina Woelm TSC) eluting with 1:6 dichloromethane: hexane, saturated with ammonia. 1-(4-Bromophenyl)-4-ethyl-2,6-dioxa-7-thiabicyclo[2,2,2]octane was obtained as colourless crystals (80 mg.). The volatile components were removed in vacuo (2.00 mm.), at 140° The residue was purified by chromatography on alumina (alumina Woelm TSC) eluting with 1:6 dichloromethane