METHODS OF MAKING OLEFINIC E- AND Z-ISOMERS

1 - 20 . (canceled)

21 . A method of making a second olefin using a first olefin, comprising steps (A) and (B):

(A) performing a metathesis reaction with the first olefin in the presence of a metal complex configured to catalyse said metathesis reaction in order to obtain a reaction mixture containing an olefin;

(B) epoxidizing the olefin contained in the reaction mixture obtained in step (A) to form an epoxide; and deoxygenizing said epoxide to form said second olefin;

wherein step (A) comprises step (Al 1):

(A11) subjecting the first olefin to a cross metathesis reaction with a fourth olefin in the presence of a metal complex to form a fifth olefin, wherein the metal complex is configured to favour the formation of the Z-isomer over the formation of the E-isomer of the fifth olefin;

and further comprising the subsequent conversion of the Z-isomer into the E-isomer to form the second olefin, wherein step (B) comprises steps (B11) to (B14):

(B11) epoxidizing said Z-isomer;

(B12) subjecting the epoxide obtained in step (B11) to hydrolysis to form a diol or to alcoholysis to form a beta-hydroxy ether;

(B13) converting the diol or beta-hydroxy ether obtained in step (B12) to a 1,3-dioxolane;

(B14) degrading the 1,3-dioxolane obtained in step (B13) to form the second olefin in the form of its E-isomer.

22 . The method of claim 21 , wherein the fourth olefin is an internal olefin.

23 . The method of claim 22 , wherein the first and fourth olefin are identical.

24 . The method of claim 22 , wherein the first and the fourth olefin are different from one another.

25 . The method of claim 21 , wherein the fourth olefin is a terminal olefin.

26 . The method of claim 25 , wherein the first and the fourth olefin are identical.

27 . The method of claim 25 , wherein the first and the fourth olefin are different from one another.

28 . The method of claim 21 , wherein the first and the fourth olefin are methyl 9-decenoate of formula 3, respectively,

and the second olefin is methyl E-9-octadecenedioate of formula 4

29 . The method of claim 21 , wherein the metal complex is selected from a compound of formula (I):

wherein

M═Mo or W

X═O or N—R 5 ;

R 1 =H;

R 2 =CMe 3 ; CMe 2 Ph; or o-C1-6-alkoxyphenyl, optionally substituted;

R 3 =substituted aryloxy, preferably substituted phenyloxy, substituted naphthyl-2-oxy or substituted 5,6,7,8-tetrahydronaphthyl-2-oxy, or substituted naphthyl-1-oxy;

R 4 =pyrrol-1-yl, 2,5-dimethylpyrrol-1-yl; or 2,5-diphenylpyrrol-1-yl; or substituted or unsubstituted indol-1-yl;

R 5 =C 6-20 aryl or C 4-10 alkyl; optionally substituted. R z =neutral ligand;

n=0 or 1;

or

from a compound of formula (II):

wherein

M═Ru;

each of R 1 and L is a neutral ligand;

r=1-3;

each of R 4 and R 5 is independently bonded to M through sulfur or oxygen; or R 4 and

R 5 are halogen, preferably Cl;

R 14 is a carbene;

or

from a compound of formula (III):

wherein

Q is a hydrocarbylene, or alkyl-substituted hydrocarbylene;

Q* forms a carbon-ruthenium bond with the carbon from the R 3 group;

X 1 is nitrate, or C 1-20 alkylcarboxylate;

R 3 is cycloalkyl or an alkyl substituted cycloalkyl group;

R 4 is an alkyl substituted aryl group;

Z is alkyl; and

R 5 , R 6 , R 7 and R 8 are hydrogen.

30 . The method of claim 29 , wherein the catalyst is selected from

(Mes=mesityl; Cy=cyclohexyl; DIPP=diisopropyphenyl; TBS=tert.-butyldimethylsilyl; mes=mesitylene; Ad=1-adamantyl; Ph=phenyl; TMS=trimethylsilyl, Me=methyl; Pr=propyl).