Process for the manufacture of compounds containing vinyl groups

Abstract

Abstract A novel process for the production of compounds of the formula A--CH═CH--D--CH═CH--A.sub.1 (I) wherein A and A 1 , independently of one another, denote phenyl, naphthyl, diphenylyl, 2-phenyl-1,2,3-triazol-4-yl or pyridyl, it being possible for A and A 1 to contain non-chromophoric substituents, and D denotes 4,4'-diphenylylene, 1,5- or 2,6-naphthylene, or a 9,10-dihydrophenanthrene or dibenzofurane radical which is bonded to the vinylene groups in the 2,7-position, which comprises reacting in a first stage a compound of the formula X--CH.sub.2 --D--CH.sub.2--X (II) wherein X denotes halogen, especially chlorine or bromine, hydroxyl or a group ##STR1## wherein X 1 represents an aliphatic cycloaliphatic or aromatic hydrocarbon radical, especially alkyl having 1 to 6 carbon atoms, or phenyl, and D has the indicated meaning, in a strongly acid medium, in a molar ratio of at least 1:2, with an organic sulphide containing 5 to 8 ring members, of the formula ##STR2## wherein B represents a polymethylene group of 4 to 7 methylene groups and wherein one of these methylene groups can be replaced by a hetero-atom and wherein these methylene groups can also contain alkyl groups with 1 to 4 carbon atoms as substituents, to give a sulphonium salt of the formula ##STR3## wherein M represents the anion of the strong acid used and n denotes the numbers 1 or 2; reacting, in a second stage, the resulting sulphonium salt with 2 mols of an aldehyde of the formula A--CHO (V) or A.sub.1 --CHO (VI) or their mixture, in the presence of strong bases, in a strongly polar, protic or aprotic, water-miscible solvent to give a diepoxide of the formula ##STR4## and subjecting in a 3rd stage, the diepoxide of the formula (VII), thus obtained, to a reduction according to processes which are in themselves known for the reduction of epoxides with elimination of the epoxide oxygen and formation of vinylene groups.

Inventors

• 👤 Hermann Rempfler
• 👤 Hans Bosshard
• 👤 Kurt Weber

Bibliographic Details