Cyclohexene oxide: 7-Oxabicyclo heptane

Propylene oxide 1,2-Epoxypropane 2-Methyloxirane 2-Methyloxacyclopropane Cyclohexene oxide 1,2-Epoxycyclohexane 7-Oxabicyclo[4.1.0]heptane ... 

In their reports on oxiranes Lewars and Rao et al have cited many of the earlier reviews. Recent work on oxiranes has been reviewed by Harvey, Sharpless and Verhoeven, Bartok and Lang, Plesni-car, Mimoun and Jorgensen. The various nomenclature systems are illustrated in the naming of (1) and (2). Cyclohexene oxide, 1,2-epoxycyclohexane and 7-oxabicyclo(4.1.0]heptane are the names used for (1) while (2) is 2,2-dimethyloxirane. 

Cyclohexene oxide (7-oxabicyclo[4.1.0]heptane]/2S6-20-47 M 98,2, b 131-133 /atm, df 0,971, ng 1,452, Fractionate the oxide through an efficient column. The main impurity is probably H2O. Dry it over MgS04, filter and distil it several times (b 129-134°/760mm). The residue is sometimes hard to remove from the distilling flask. To avoid this difficulty, add a small amount of a mixture of ground NaCl and Celite (1 1) to help break up the residue particularly if H2O is added. [Osterberg Org Synth Coll Vol I 185 1948, Beilstein 17 H 21, 17/1 V 203.]... 

The preparation of cyclohexene sulfide (7-thiobicyclo [4.1.0 Jheptane)378 3 82 may be described as an example Cyclohexene oxide (7-oxabicyclo[4.1.0]heptane) (5 g) in methanol (20 ml) is treated with thiourea (5 g) at 60° for 1.5 h. The mixture is poured into water (150ml) and extracted with chloroform. Fractionation affords the sulfide, b.p. 67-68716 mm, in 58% yield. 

Cyclohexene oxide (7-oxabicyclo-[4.1.0] heptane, cyclohexene epoxide, cyclohexane oxide, 1,2-epoxycyclo-hexane, tetramethy-lene oxirane) [286-20-4]... 

CAS 286-20-4 EINECS/ELINCS 206-007-7 Synonyms Bicycle [4.1.0] heptane, 7-oxa- CCHO Cyclohexane, 1,2-epoxy- Cyclohexane oxide Cyclohexene epoxide Cyclohexene-1-oxide 1,2-Cyclohexene oxide Cyclohexylene oxide Epoxycyclohexane 1,2-Epoxycyclohexane 7-Oxabicyclo [4.1.0] heptane Tetramethyleneoxirane Empirical CeHioO... 

C 156 Cyclohexene oxide. See 7-Oxabicyclo[4 10]heptane. C157 Cyclohexene sulfide. See 7-Thiabicyclo[4 l 0]heptane. 

Epoxyeyclohexanone has been prepared in 30% yield4 by epoxi-dation of 2-cyclohexen-l-one with alkaline hydrogen peroxide, using a procedure described for isophorone oxide (4,4,6-trimethyl-7-oxabicyclo[4.1.0]heptan-2-one).5 A better yield (66%) was obtained using f r/-butyl hydroperoxide (1,1-dimethylethylhydroperoxide) and Triton B in benzene solution.6 The procedure described here is simple and rapid. 

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