Furfural,
toluene, dimethyl sulfoxide, acetic
acid, anhydrous tetrahydrofuran, hydrochloric acid, ethylene diamine,
dichloromethane, m-cresol, and deuterated chloroform
were purchased from Kanto Kagaku Co., Inc. (Tokyo, Japan). p-Toluenesulfonic acid, 1,3-propanediamine, 1,4-butanediamine,
1,5-pentanediamine, and 1,6-hexanediamine were purchased from Tokyo
Chemical Industry Co., Ltd. (Tokyo, Japan). Palladium diacetate and
ethylene glycol were purchased from Sigma-Aldrich Japan Co., LLC.
(Tokyo, Japan). Furfural was used after distillation from Na2CO3 under reduced pressure. Acetic acid was distilled,
and m-cresol was distilled under reduced pressure.
Toluene, dichloromethane, dimethyl sulfoxide, and ethylene glycol
were distilled from calcium hydride before use. Ethylenediamine, 1,3-propanediamine,
1,4-butanediamine, and 1,5-pentanediamine were distilled over 4 Å
molecular sieves. 1,6-hexanediamine and p-phenylenediamine
were sublimed under reduced pressure. All the other chemicals were
of reagent grade and used without further purification.
toluene, dimethyl sulfoxide, acetic
acid, anhydrous tetrahydrofuran, hydrochloric acid, ethylene diamine,
dichloromethane, m-cresol, and deuterated chloroform
were purchased from Kanto Kagaku Co., Inc. (Tokyo, Japan). p-Toluenesulfonic acid, 1,3-propanediamine, 1,4-butanediamine,
1,5-pentanediamine, and 1,6-hexanediamine were purchased from Tokyo
Chemical Industry Co., Ltd. (Tokyo, Japan). Palladium diacetate and
ethylene glycol were purchased from Sigma-Aldrich Japan Co., LLC.
(Tokyo, Japan). Furfural was used after distillation from Na2CO3 under reduced pressure. Acetic acid was distilled,
and m-cresol was distilled under reduced pressure.
Toluene, dichloromethane, dimethyl sulfoxide, and ethylene glycol
were distilled from calcium hydride before use. Ethylenediamine, 1,3-propanediamine,
1,4-butanediamine, and 1,5-pentanediamine were distilled over 4 Å
molecular sieves. 1,6-hexanediamine and p-phenylenediamine
were sublimed under reduced pressure. All the other chemicals were
of reagent grade and used without further purification.