The invention relates to the manufacture of certain polyunsaturated compounds employing a particular application of the Mitsonobu reaction in the presence of at least one anti-oxidant. We have found a method of making a pharmaceutically-acceptable polyunsaturated ester or thioester compound directly, which can ultimately be converted to the advantageous ketone compounds, in which unwanted oxidation and cis/trans isomerization are substantially reduced or eliminated using particular Mitsonobu chemistry.

A method of producing an organopolysulfide or salt thereof is provided which includes a step of mixing an organomonosulfide or salt thereof and elemental sulfur, wherein the mixing is carried out at a temperature not greater than 95 C and in the absence of any added liquid phase for a time effective to produce the organopolysulfide or salt thereof. The described method makes possible the preparation of organopolysulfides and organopolysulfide salts without the use of solvent or catalyst.

A method of producing an organopolysulfide or salt thereof is provided which includes a step of mixing an organomonosulfide or salt thereof and elemental sulfur, wherein the mixing is carried out at a temperature not greater than 95 C and in the absence of any added liquid phase for a time effective to produce the organopolysulfide or salt thereof. The described method makes possible the preparation of organopolysulfides and organopolysulfide salts without the use of solvent or catalyst.

A method of producing an organopolysulfide or salt thereof is provided which includes a step of mixing an organomonosulfide or salt thereof and elemental sulfur, wherein the mixing is carried out at a temperature not greater than 95 C and in the absence of any added liquid phase for a time effective to produce the organopolysulfide or salt thereof. The described method makes possible the preparation of organopolysulfides and organopolysulfide salts without the use of solvent or catalyst.

According to the present invention, it is possible to provide a polythiol composition, which comprises a polythiol (A) represented by formula (1) and a thiol compound (B) represented by formula (2). ##STR00001##
(In formula (1), p and q each independently represent an integer of 1 to 3.) ##STR00002##
(In formula (2), p and q each independently represent an integer of 1 to 3.)

According to the present invention, it is possible to provide a polythiol composition, which comprises a polythiol (A) represented by formula (1) and a thiol compound (B) represented by formula (2). ##STR00001##
(In formula (1), p and q each independently represent an integer of 1 to 3.) ##STR00002##
(In formula (2), p and q each independently represent an integer of 1 to 3.)

A method of producing an organopolysulfide or salt thereof is provided which includes a step of mixing an organomonosulfide or salt thereof and elemental sulfur, wherein the mixing is carried out at a temperature not greater than 95 C and in the absence of any added liquid phase for a time effective to produce the organopolysulfide or salt thereof. The described method makes possible the preparation of organopolysulfides and organopolysulfide salts without the use of solvent or catalyst.

A method of producing an organopolysulfide or salt thereof is provided which includes a step of mixing an organomonosulfide or salt thereof and elemental sulfur, wherein the mixing is carried out at a temperature not greater than 95 C and in the absence of any added liquid phase for a time effective to produce the organopolysulfide or salt thereof. The described method makes possible the preparation of organopolysulfides and organopolysulfide salts without the use of solvent or catalyst.

According to the present invention, it is possible to provide a polythiol composition, which comprises a polythiol (A) represented by formula (1) and a thiol compound (B) represented by formula (2).

##STR00001##

(In formula (1), p and q each independently represent an integer of 1 to 3.)

##STR00002##

(In formula (2), p and q each independently represent an integer of 1 to 3.)

According to the present invention, it is possible to provide a polythiol composition, which comprises a polythiol (A) represented by formula (1) and a thiol compound (B) represented by formula (2).

##STR00001##

(In formula (1), p and q each independently represent an integer of 1 to 3.)

##STR00002##

(In formula (2), p and q each independently represent an integer of 1 to 3.)