(R)-2-(but-3-en-1-yl)oxirane

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 100 mL round-bottom flask were placed 8.5 mL of 5,6-epoxy-1-hexene (0.1 moles), 1.5 equivalents of trimethoxysilane (17 mL), 30 mL of toluene dried by refluxing with sodium benzophenone ketyl, and 3 mg of tris(triphenylphosphine)rhodium (I) chloride. The resulting light purple solution was stirred and heated at 80° C. for 12 hours. The solvent was removed under reduced pressure, and the resulting oil subjected to fractional vacuum distillation. 5,6-Epoxyhexyltrimethoxysilane was obtained (13.5 g, 61% yield) as a colorless liquid. In a 100 mL round-bottom flask were placed The solvent was removed under reduced pressure the resulting oil subjected to fractional vacuum distillation

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

Procedure: 27.6 g of diphenylsilane (0.15 mole) were dispersed in 100 g toluene with 0.02 g rhodiumtrichloride hydrate (as a solution in 0.5 cc ethanol) then the solution was brought to 100° C. when 32 g 1,2-epoxy-5-hexene (0.32 mole) were added dropwise. A two hour hold at 100°-110° followed, which consumed all SiH per IR analysis. Solvent was distilled off leaving 45 g residue as a mobile, 15 cstk viscosity fluid product, nD25 =1.5532. Infrared analysis was consistent with the proposed structure, with evidence of siloxane by products also present. was brought to 100° C. were added dropwise A two hour hold at 100°-110° which consumed all SiH per IR analysis Solvent was distilled off

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

Procedure: 27.6 g of diphenylsilane (0.15 mole) were dispersed in 100 g toluene with 0.02 g rhodiumtrichloride hydrate (as a solution in 0.5 cc ethanol) then the solution was brought to 100° C. when 32 g 1,2-epoxy-5-hexene (0.32 mole) were added dropwise. A two hour hold at 100°-110° followed, which consumed all SiH per IR analysis. Solvent was distilled off leaving 45 g residue as a mobile, 15 cstk viscosity fluid product, nD25 =1.5532. Infrared analysis was consistent with the proposed structure, with evidence of siloxane by products also present. was brought to 100° C. were added dropwise A two hour hold at 100°-110° which consumed all SiH per IR analysis Solvent was distilled off

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 100 mL round-bottom flask were placed 8.5 mL of 5,6-epoxy-1-hexene (0.1 moles), 1.5 equivalents of trimethoxysilane (17 mL), 30 mL of toluene dried by refluxing with sodium benzophenone ketyl, and 3 mg of tris(triphenylphosphine)rhodium (I) chloride. The resulting light purple solution was stirred and heated at 80° C. for 12 hours. The solvent was removed under reduced pressure, and the resulting oil subjected to fractional vacuum distillation. 5,6-Epoxyhexyltrimethoxysilane was obtained (13.5 g, 61% yield) as a colorless liquid. In a 100 mL round-bottom flask were placed The solvent was removed under reduced pressure the resulting oil subjected to fractional vacuum distillation

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 100 mL round-bottom flask were placed 8.5 mL of 5,6-epoxy-1-hexene (0.1 moles), 1.5 equivalents of trimethoxysilane (17 mL), 30 mL of toluene dried by refluxing with sodium benzophenone ketyl, and 3 mg of tris(triphenylphosphine)rhodium (I) chloride. The resulting light purple solution was stirred and heated at 80° C. for 12 hours. The solvent was removed under reduced pressure, and the resulting oil subjected to fractional vacuum distillation. 5,6-Epoxyhexyltrimethoxysilane was obtained (13.5 g, 61% yield) as a colorless liquid. In a 100 mL round-bottom flask were placed The solvent was removed under reduced pressure the resulting oil subjected to fractional vacuum distillation

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

Procedure: 27.6 g of diphenylsilane (0.15 mole) were dispersed in 100 g toluene with 0.02 g rhodiumtrichloride hydrate (as a solution in 0.5 cc ethanol) then the solution was brought to 100° C. when 32 g 1,2-epoxy-5-hexene (0.32 mole) were added dropwise. A two hour hold at 100°-110° followed, which consumed all SiH per IR analysis. Solvent was distilled off leaving 45 g residue as a mobile, 15 cstk viscosity fluid product, nD25 =1.5532. Infrared analysis was consistent with the proposed structure, with evidence of siloxane by products also present. was brought to 100° C. were added dropwise A two hour hold at 100°-110° which consumed all SiH per IR analysis Solvent was distilled off

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: The cross metathesis of (±)-2-(but-3-enyl)oxirane (3.80 g, 38.7 mmol) with ethyl allyl ether (10.0 g, 116 mmol) was performed as described previously in Example 9.2, Step A to give (±)-2-(5-ethoxypent-3-enyl)oxirane as an inseparable mixture of olefin isomers (trans:cis=10:1) after silica gel chromatography. 1H NMR (400 MHz, CDCl3): trans isomer: δ 5.73 (1H, m), 5.63 (1H, m), 3.91 (2H, m), 3.48 (2H, q, J=7.0 Hz), 2.93 (1H, m), 2.75 (1H, m), 2.48 (1H, dd, J=5.0, 2.7 Hz), 2.22 (2H, m), 1.63 (2H, m), 1.21 (3H, t, J=7.0 Hz). cis isomer: δ 5.62 (2H, m), 4.04 (2H, m), 3.48 (2H, q, J=7.0 Hz), 2.93 (1H, m), 2.75 (1H, m), 2.49 (1H, m), 2.22 (2H, m), 1.63 (2H, m), 1.22 (3H, t, J=7.0 Hz).

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

Procedure: 2-(But-3-enyl)oxirane (1.000 g, 10.2 mmol) and hex-1-ene (9.12 g, 102 mmol) were stirred at room temperature for 24 hr in a sealed scintillation vial with Zhan Catalyst-1 (0.057 g, 0.086 mmol). Solvent was removed under reduced pressure and the residue purified by column chromatography (0-10% EtOAc/n-hexane/silica) to give (±)-(E)-2-(oct-3-enyl)oxirane as a colorless oil. 1H NMR (CDCl3): δ 5.5-5.4 (m, 2H), 3.0-2.9 (m, 1H), 2.8-2.7 (m, 1H), 2.5-2.45 (m, 1H), 2.2-2.1 (m, 2H), 1.99 (q, 2H, J=5.7), 1.65-1.55 (m, 2H), 1.35-1.25 (m, 4H), 0.95-0.85 (m, 3H). Contains ca 20% (Z)-2-(oct-3-enyl)oxirane. Solvent was removed under reduced pressure the residue purified by column chromatography (0-10% EtOAc/n-hexane/silica)

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

Procedure: 2-(But-3-enyl)oxirane (1.000 g, 10 mmol) and 2-methylbut-2-ene (10 g, 102 mmol) were stirred at room temperature for 24 hr in a sealed scintillation vial with Zhan catalyst 1 (0.057 g, 0.086 mmol). Solvent was removed under reduced pressure and the residue purified by column chromatography (0-10% EtOAc/n-hexane/silica) to give 2-(4-methylpent-3-enyl)oxirane as a colorless oil. 1H NMR (CDCl3): δ 5.2-5.1 (m, 1H), 2.95-2.88 (m, 1H), 2.75 (dd, 1H J1=5.0, J2=4.1), 2.48 (dd, 1H J1=5.0, J2=2.8), 2.15 (2H, q, J=7.4), 1.70 (s, 3H), 1.63 (s, 3H), 1.60-1.50 (m, 2H). Solvent was removed under reduced pressure the residue purified by column chromatography (0-10% EtOAc/n-hexane/silica)

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

Procedure: The cross metathesis of (±)-2-(but-3-enyl)oxirane (3.80 g, 38.7 mmol) with ethyl allyl ether (10.0 g, 116 mmol) was performed as described previously in Example 9.2, Step A to give (±)-2-(5-ethoxypent-3-enyl)oxirane as an inseparable mixture of olefin isomers (trans:cis=10:1) after silica gel chromatography. 1H NMR (400 MHz, CDCl3): trans isomer: δ 5.73 (1H, m), 5.63 (1H, m), 3.91 (2H, m), 3.48 (2H, q, J=7.0 Hz), 2.93 (1H, m), 2.75 (1H, dd, J=5.0, 2.7 Hz), 2.22 (2H, m), 1.63 (2H, m), 1.21 (3H, t, J=7.0 Hz). cis isomer: δ 5.62 (2H, m), 4.04 (2H, m), 3.48 (2H, q, J=7.0 Hz), 2.93 (1H, m), 2.75 (1H, m), 2.49 (1H, m), 2.22 (2H, m), 1.63 (2H, m), 1.22 (3H, t, J=7.0 Hz).