Mixtures of aryl oxabicyclooctane derivatives, mixtures of phenyl norbornane derivatives, processes for preparing same, perfumery uses thereof and intermediates used in said processes

A process for preparing an aryl oxabicyclooctane derivative or a phenyl norbornane derivative or a phenyl norbornane derivative comprising the steps of carrying out the reaction:

• ##STR182## wherein X represents chloro or bromo followed by the reaction:
• ##STR183## wherein M represents 0, 1 or 2;
• D represents a cyclizing reagent selected from the group consisting of (i) mixtures of a C.sub.1 -C.sub.2 nitroalkane and methane sulfonic acid and (ii) mixtures of borontrifluoride diethyl etherate and a C.sub.1 -C.sub.2 nitroalkane;
• wherein G.sub.1 represents a mixture of compounds having the structures:
• ##STR184## with N and P being the same and being 1 or 2;
• wherein G.sub.2 represents a mixture of compounds having the structures:
• ##STR185## with the provisos that when M is 1 or 2, then the term [G.sub.1 or G.sub.2 ] represents a mixture of compounds defined according to the structures:
• ##STR186## the cyclization agent D being a mixture of a C.sub.1 -C.sub.2 nitroalkane and methane sulfonic acid;
• the reaction temperature being in the range of from about 60.degree. C. up to about 90.degree. C. for a period of time of from about three hours up to about ten hours and when M is 0 then the term [G.sub.1 or G.sub.2 ] is a mixture of compounds having the structures:
• ##STR187## and the cyclization agent D is a mixture of boron trifluoride diethyl etherate, and a C.sub.1 -C.sub.2 nitroalkane, the reaction temperature being in the range of from about 60.degree. C. up to about 90.degree. C. for a period of time of from about three hours up to about ten hours.