2,6,6-trimethylbicyclo[3.1.1]heptane

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

Procedure: Hypochlorite treatment of the α-pinene raised the chloride level to about 100 ppm (as elemental chloride) based on pinene feed. Hydrogenation of this pinene was fast and yielded a good ratio (96.8/3.2). Reuse of the catalyst heel went quickly with a slightly reduced ratio, when used at either the 3% level or 1% level. Repoisoning (1/2% sodium hypochlorite-treated α-pinene) was achieved by mixing hypochlorite-treated feed with fresh α-pinene and yielded pinane with a 97.5/2.5 cis-:trans- ratio. A ratio of 98.1/1.9 was achieved in 30 hours' reaction at a lower temperature of about 30° C. using hypochlorite-treated feed.

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

Procedure: To 25 milliliters of acetonitrile were added 1.38 grams (10 millimoles) of pinane, 0.13 gram (0.8 millimole) of N-hydroxyphthalimide and 0.015 gram (0.06 millimole) of Co(AA)2, and the resultant mixture was stirred in an oxygen atmosphere at a temperature of 100° C. for six hours. Pinane was transformed into 2-pinanol (selectivity for pinane 91%, yield 82%) with a transformation rate of 90%.

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

Procedure: To 25 milliliters of acetonitrile were added 1.38 grams (10 millimoles) of pinane, 0.13 gram (0.8 millimole) of N-hydroxyphthalimide and 0.015 gram (0.06 millimole) of Co(AA)2, and the resultant mixture was stirred in an oxygen atmosphere at a temperature of 100° C. for six hours. Pinane was transformed into 2-pinanol (selectivity for pinane 91%, yield 82%) with a transformation rate of 90%.

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

Procedure: Hypochlorite treatment of the α-pinene raised the chloride level to about 100 ppm (as elemental chloride) based on pinene feed. Hydrogenation of this pinene was fast and yielded a good ratio (96.8/3.2). Reuse of the catalyst heel went quickly with a slightly reduced ratio, when used at either the 3% level or 1% level. Repoisoning (1/2% sodium hypochlorite-treated α-pinene) was achieved by mixing hypochlorite-treated feed with fresh α-pinene and yielded pinane with a 97.5/2.5 cis-:trans- ratio. A ratio of 98.1/1.9 was achieved in 30 hours' reaction at a lower temperature of about 30° C. using hypochlorite-treated feed.

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

Procedure: To 25 milliliters of acetonitrile were added 1.38 grams (10 millimoles) of pinane, 0.13 gram (0.8 millimole) of N-hydroxyphthalimide and 0.015 gram (0.06 millimole) of Co(AA)2, and the resultant mixture was stirred in an oxygen atmosphere at a temperature of 100° C. for six hours. Pinane was transformed into 2-pinanol (selectivity for pinane 91%, yield 82%) with a transformation rate of 90%.

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

Procedure: Hypochlorite treatment of the α-pinene raised the chloride level to about 100 ppm (as elemental chloride) based on pinene feed. Hydrogenation of this pinene was fast and yielded a good ratio (96.8/3.2). Reuse of the catalyst heel went quickly with a slightly reduced ratio, when used at either the 3% level or 1% level. Repoisoning (1/2% sodium hypochlorite-treated α-pinene) was achieved by mixing hypochlorite-treated feed with fresh α-pinene and yielded pinane with a 97.5/2.5 cis-:trans- ratio. A ratio of 98.1/1.9 was achieved in 30 hours' reaction at a lower temperature of about 30° C. using hypochlorite-treated feed.