Reaktion #790436

Reaktionsgleichung

methyl sulfide

trans-(Z)-1-methyl-4-(1,5-dimethyl-1,4-hexadienyl)-1,2-epoxycyclohexane

O3

→

1-methyl-4-acetyl-1,2-epoxycyclohexane

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeCompounds 8 and 9 were deoxygenated after the procedure of Delay and Ohloff, supra
2. 2
   Sonstigeas a mixture, produced a single new compound
3. 3
   SonstigeDeoxygenation of isolated 9 (>80% purity)
4. 4
   Sonstigeproduced a single compound
5. 5
   SonstigeOzonolysis of isolated 9

Vorschrift

Compounds 8 and 9 were deoxygenated after the procedure of Delay and Ohloff, supra. These compounds dexoygenated (FIG. 1) individually or as a mixture, produced a single new compound that coeluted with 6 and matched the MS of synthetic 6. Isolated components in ca. 100 μl of CH2Cl2 were ozonized by addition of 100 μl of O3 -saturated CH2Cl2 at -78° C. (8341 Matheson Laboratory Ozonator), and ozonides were cleaved with methyl sulfide (30 μl; 40 μl/μl CH2Cl2). Compounds 12 and 13 (1-methyl-4-acetyl-1,2-epoxycyclohexane) were synthesized by standard methods and structurally verified by spectral comparisons to published values for these isomers. Ozonolysis of compounds 8 and 9 together produced ozonides 12 and 13 (FIG. 1) in approximately the same ratio as the ratio of 8:9 in airborne-trapped samples. Thus, compound 8 is trans-(Z)-1-methyl-4-(1,5-dimethyl-1,4-hexadienyl)-1,2-epoxycyclohexane. Deoxygenation of isolated 9 (>80% purity) produced a single compound having a GC-retention time and MS identical to synthetic 6 (FIG. 1). Ozonolysis of isolated 9 produced 13, but did not produce 12. Thus, component 9 is cis-(Z)-1-methyl-4-(1,5-dimethyl-1,4-hexadienyl)-1,2-epoxycyclohexane.

Quelle