Carbon Dioxide → Octyl isocyanate

Participants

Reaction Steps

A Fischer-Porter bottle was charged with 0.55 g (4.2 mmol) of octyl amine, 0.99 g of P1 tBu (3 mmol), 25 mL of acetonitrile and 130 mg (0.84 mmol) of tridecane as an internal standard. The bottle was pressurized to 80 psig with carbon dioxide and the solution was stirred for 30 min. at room temperature. A second Ficher-Porter bottle was charged with 0.65 g (4.7 mmol) of sulfur trioxide trimethylamine adduct (SO3 -NMe3) and 20 mL of acetonitrile then pressurized to 80 psig with CO2. The two solutions were cooled to 0° C. in an ice bath for 10 min after which time the octyl carbamate solution was added rapidly to the SO3 -NMe3 suspension. An aliquot was taken after five minutes and diluted with diethyl ether prior to G.C. analysis which indicated a yield of 11% octyl isocyanate. Further monitoring of the reaction progress over 48 hrs gave a maximum yield of 27% octyl isocyanate.

Provenance & Evidence