The present invention relates to a process for preparing a (1S,2R)-(2-hydroxy-3,5,5-trimethyl-3-cyclopentenyl)methyl carboxylate compound of the following general formula (S,R)-(2), wherein R.sup.1 represents a monovalent hydrocarbon group having 1 to 6 carbon atoms, and a bold wedged bond represents the absolute configuration, and a (1R,2S)-(2-acetoxy-3,5,5-trimethyl-3-cyclopentenyl)methyl carboxylate compound of the following general formula (R,S)-(3), wherein R.sup.1 is as defined above, a hashed wedged bond represents the absolute configuration, and Ac represents an acetyl group, the process comprising: subjecting a (1RS,2SR)-(2-hydroxy-3,5,5-trimethyl-3-cyclopentenyl)methyl carboxylate compound of the following general formula (RS,SR)-(2), wherein R.sup.1 is as defined above, and a hashed unwedged bond represents a relative configuration, to a kinetic resolution reaction with a lipase in the presence of vinyl acetate to obtain the (1S,2R)-(2-hydroxy-3,5,5-trimethyl-3-cyclopentenyl)methyl carboxylate compound ((S,R)-(2)) and the (1R,2S)-(2-acetoxy-3,5,5-trimethyl-3-cyclopentenyl)methyl carboxylate compound ((R,S)-(3)). ##STR00001##

The present invention relates to a process for preparing a (1S,2R)-(2-hydroxy-3,5,5-trimethyl-3-cyclopentenyl)methyl carboxylate compound of the following general formula (S,R)-(2), wherein R.sup.1 represents a monovalent hydrocarbon group having 1 to 6 carbon atoms, and a bold wedged bond represents the absolute configuration, and a (1R,2S)-(2-acetoxy-3,5,5-trimethyl-3-cyclopentenyl)methyl carboxylate compound of the following general formula (R,S)-(3), wherein R.sup.1 is as defined above, a hashed wedged bond represents the absolute configuration, and Ac represents an acetyl group, the process comprising: subjecting a (1RS,2SR)-(2-hydroxy-3,5,5-trimethyl-3-cyclopentenyl)methyl carboxylate compound of the following general formula (RS,SR)-(2), wherein R.sup.1 is as defined above, and a hashed unwedged bond represents a relative configuration, to a kinetic resolution reaction with a lipase in the presence of vinyl acetate to obtain the (1S,2R)-(2-hydroxy-3,5,5-trimethyl-3-cyclopentenyl)methyl carboxylate compound ((S,R)-(2)) and the (1R,2S)-(2-acetoxy-3,5,5-trimethyl-3-cyclopentenyl)methyl carboxylate compound ((R,S)-(3)). ##STR00001##

Processes for converting a hydrocarbon reactant into an alcohol compound and/or a carbonyl compound are disclosed in which the hydrocarbon reactant and either a supported chromium (VI) catalyst or a supported chromium (II) catalyst are contacted, optionally with UV-visible light irradiation, followed by exposure to an oxidizing atmosphere and then hydrolysis to form a reaction product containing the alcohol compound and/or the carbonyl compound. The presence of oxygen significant increases the amount of alcohol/carbonyl product formed, as well as the formation of oxygenated dimers and trimers of certain hydrocarbon reactants.

Processes for converting a hydrocarbon reactant into an alcohol compound and/or a carbonyl compound are disclosed in which the hydrocarbon reactant and either a supported chromium (VI) catalyst or a supported chromium (II) catalyst are contacted, optionally with UV-visible light irradiation, followed by exposure to an oxidizing atmosphere and then hydrolysis to form a reaction product containing the alcohol compound and/or the carbonyl compound. The presence of oxygen significant increases the amount of alcohol/carbonyl product formed, as well as the formation of oxygenated dimers and trimers of certain hydrocarbon reactants.

Embodiments of a system and method are disclosed for obtaining high-energy fuels. In some embodiments, the system and method produces one or more fused cyclic compounds that can include one or more bridging points. The fused cyclic compounds are suitable for use as a high-energy fuels, and may be derived from biomass.

Embodiments of a system and method are disclosed for obtaining high-energy fuels. In some embodiments, the system and method produces one or more fused cyclic compounds that can include one or more bridging points. The fused cyclic compounds are suitable for use as a high-energy fuels, and may be derived from biomass.

Embodiments of a system and method are disclosed for obtaining high-energy fuels. In some embodiments, the system and method produces one or more fused cyclic compounds that can include one or more bridging points. The fused cyclic compounds are suitable for use as a high-energy fuels, and may be derived from biomass.

Embodiments of a system and method are disclosed for obtaining high-energy fuels. In some embodiments, the system and method produces one or more fused cyclic compounds that can include one or more bridging points. The fused cyclic compounds are suitable for use as a high-energy fuels, and may be derived from biomass.

Control or repellency of bed bugs is accomplished by bringing the bed bugs into contact with at least one of the compounds of the structure (I) ##STR00001##
Wherein
R is selected from —OH, —OC(O)R.sub.4, —OR.sub.6, —(OR.sub.6).sub.2, wherein each R.sub.6 is independently selected from an alkyl group containing from 1 to 4 carbon atoms and R.sub.4 is a branched or straight chain saturated or unsaturated hydrocarbyl group with zero to two double bonds and from 1 to 15 carbon atoms;
X is O or CH.sub.2, with the proviso that when X is O, R can only be ═O;
each Z is independently selected from (CH) and (CH.sub.2)
y is a numeral selected from 1 and 2;
R.sub.1 is selected from H or a branched or straight chain saturated or unsaturated hydrocarbyl group with zero to two double bonds and from 1 to 15 carbon atoms.
R.sub.2 is selected from H and a branched or straight chain saturated or unsaturated hydrocarbyl group with zero to three double bonds and from 1 to 15 carbon atoms.
R.sub.3 is selected from H, a branched or straight chain, saturated or unsaturated hydrocarbyl group with zero to three double bonds and from 1 to 15 carbon atoms, —(CH.sub.2).sub.nOH, —C(O)OR.sub.5, —CH.sub.2C(O)OR.sub.7, —CH.sub.2C(O)R.sub.8, —C(O)NR.sub.9R.sub.10, —CH.sub.2C(O)NR.sub.11R.sub.12 where each of R.sub.5, R.sub.7, R.sub.8, R.sub.9, R.sub.10, R.sub.11 and R.sub.12 is independently selected from H and a branched or straight chain, saturated or unsaturated hydrocarbyl group with zero to three double bonds and from 1 to 15 carbon atoms, and n is an integer of from 1 to 12; and
the bond between the 2 and 3 positions in the ring structure may be a single or a double bond, and wherein the compounds of structure (1) contain from 11 to 20 total carbon atoms, except where R is ═O, X═CH.sub.2 and y is 1 the compounds of structure (I) contain from 13 to 20 total carbon atoms in the compounds. wherein the compounds of structure (1) contain from 11 to 20 total carbon atoms, except where R is ═O, X═CH.sub.2 and y is 1 the compounds of structure (I) contain from 13 to 20 total carbon atoms in the compounds. wherein the compounds of structure (1) contain from 11 to 20 total carbon atoms, except where R is ═O, X═CH.sub.2 and y is 1 the compounds of structure (I) contain from 13 to 20 total carbon atoms in the compounds.

Control or repellency of bed bugs is accomplished by bringing the bed bugs into contact with at least one of the compounds of the structure (I) ##STR00001##
Wherein
R is selected from —OH, —OC(O)R.sub.4, —OR.sub.6, —(OR.sub.6).sub.2, wherein each R.sub.6 is independently selected from an alkyl group containing from 1 to 4 carbon atoms and R.sub.4 is a branched or straight chain saturated or unsaturated hydrocarbyl group with zero to two double bonds and from 1 to 15 carbon atoms;
X is O or CH.sub.2, with the proviso that when X is O, R can only be ═O;
each Z is independently selected from (CH) and (CH.sub.2)
y is a numeral selected from 1 and 2;
R.sub.1 is selected from H or a branched or straight chain saturated or unsaturated hydrocarbyl group with zero to two double bonds and from 1 to 15 carbon atoms.
R.sub.2 is selected from H and a branched or straight chain saturated or unsaturated hydrocarbyl group with zero to three double bonds and from 1 to 15 carbon atoms.
R.sub.3 is selected from H, a branched or straight chain, saturated or unsaturated hydrocarbyl group with zero to three double bonds and from 1 to 15 carbon atoms, —(CH.sub.2).sub.nOH, —C(O)OR.sub.5, —CH.sub.2C(O)OR.sub.7, —CH.sub.2C(O)R.sub.8, —C(O)NR.sub.9R.sub.10, —CH.sub.2C(O)NR.sub.11R.sub.12 where each of R.sub.5, R.sub.7, R.sub.8, R.sub.9, R.sub.10, R.sub.11 and R.sub.12 is independently selected from H and a branched or straight chain, saturated or unsaturated hydrocarbyl group with zero to three double bonds and from 1 to 15 carbon atoms, and n is an integer of from 1 to 12; and
the bond between the 2 and 3 positions in the ring structure may be a single or a double bond, and wherein the compounds of structure (1) contain from 11 to 20 total carbon atoms, except where R is ═O, X═CH.sub.2 and y is 1 the compounds of structure (I) contain from 13 to 20 total carbon atoms in the compounds. wherein the compounds of structure (1) contain from 11 to 20 total carbon atoms, except where R is ═O, X═CH.sub.2 and y is 1 the compounds of structure (I) contain from 13 to 20 total carbon atoms in the compounds. wherein the compounds of structure (1) contain from 11 to 20 total carbon atoms, except where R is ═O, X═CH.sub.2 and y is 1 the compounds of structure (I) contain from 13 to 20 total carbon atoms in the compounds.