Inclusion complex compound, process for its production, and method for its use

An inclusion complex compound comprising (a) meta-cyclophane of the formula ##STR14## and (b) a trans-terpenoid of the formula ##STR15## wherein n is an integer of 1 to 5;

• A.sub.1 and A.sub.2 each represent --H, --Cl, --Br, --OH, --NH.sub.2, --NO.sub.2, --SH, --SO.sub.3 H, --CH.sub.3, --OR, ##STR16## --NHR, or --SR in which R is an alkyl group containing 1 to 5 carbon atoms;
• these atoms or groups may be bonded to a carbon atom through an alkylene group, in which case the number of carbon atoms of the alkylene group and that of carbon atoms of the group R is not more than 5;
• and C* is the carbon atom of a carbonyl or methylene group,
• included by the meta-cyclophane.

A process for separating a trans-terpenoid from a mixture containing it, which comprises contacting meta-cyclophane of the formula ##STR19## with a trans-terpenoid of the formula ##STR20## wherein n is an integer of 1 to 9;

• A.sub.1 and A.sub.2 each represent (1) a hydrogen atom, (2) a halogen atom, (3) an inorganic group containing an oxygen, nitrogen or sulfur atom, (4) an organic group containing 1 to 5 carbon atoms, or (5) an organic group containing an oxygen, nitrogen or
• sulfur atom and 1 to 5 carbon atoms;
• and C* is
• the carbon atom of a carbonyl or methylene group, to form an inclusion complex compound comprising the meta-cyclophane and the trans-terpenoid included by it, separating the inclusion complex compound from the mixture, and then separating the included trans-terpenoid from the inclusion complex compound.

A process for producing an inclusion complex compound which comprises contacting metacyclophane of the formula:

• ##STR21## with a mixture containing a trans-terpenoid of the formula:
• ##STR22## wherein n is an integer of 1 to 9;
• A.sub.1 and A.sub.2 each represent (1) a hydrogen atom, (2) a halogen atom, (3) an inorganic group containing an oxygen, nitrogen or sulfur atom, (4) an organic group containing 1 to 5 carbon atoms;
• and C* is the carbon atom of a carbonyl or methylene group,
• to form an inclusion complex compound comprising the metacyclophane and the trans-terpenoid included by it, and then separating the inclusion complex compound from the mixture.