The invention relates to processes for preparing benzoprostacyclin analogues and intermediates prepared from the process, and the benzoprostacyclin analogues prepared therefrom. The invention also relates to cyclopentenone intermediates in racemic or optically active form.

The invention relates to processes for preparing benzoprostacyclin analogues and intermediates prepared from the process, and the benzoprostacyclin analogues prepared therefrom. The invention also relates to cyclopentenone intermediates in racemic or optically active form.

An iodine-containing (meth)acrylate compound represented by formula (1):

##STR00001##

wherein R.sup.1 represents a hydrogen atom, methyl, or halogen; each R.sup.2 independently represents a hydrogen atom, a linear organic group having 1 to 20 carbon atoms, a branched organic group having 3 to 20 carbon atoms, or a cyclic organic group having 3 to 20 carbon atoms; A represents an organic group having 1 to 30 carbon atoms; A contains at least one acyl group; n.sup.1 represents 0 or 1; and n.sup.2 represents an integer of 1 to 20.

An iodine-containing (meth)acrylate compound represented by formula (1):

##STR00001##

wherein R.sup.1 represents a hydrogen atom, methyl, or halogen; each R.sup.2 independently represents a hydrogen atom, a linear organic group having 1 to 20 carbon atoms, a branched organic group having 3 to 20 carbon atoms, or a cyclic organic group having 3 to 20 carbon atoms; A represents an organic group having 1 to 30 carbon atoms; A contains at least one acyl group; n.sup.1 represents 0 or 1; and n.sup.2 represents an integer of 1 to 20.

The present invention provides a process for preparing 6-isopropenyl-3-methyl-9-decenyl acetate (5): wherein Ac represents an acetyl group, the process comprising steps of: subjecting a 2-methyl-2,6-heptadiene compound (1) having a leaving group X at position 1: wherein X represents an acyloxy group having 1 to 10 carbon atoms including the carbon atom of the carbonyl group, an alkanesulfonyloxy group having 1 to 10 carbon atoms, an arenesulfonyloxy group having 6 to 20 carbon atoms, or a halogen atom, to a nucleophilic substitution reaction with a 3-methylpentyl nucleophilic reagent (2) having a protected hydroxyl group at position 5: wherein M represents Li, MgZ.sup.1, ZnZ.sup.1, Cu, CuZ.sup.1, or CuLiZ.sup.1, wherein Z.sup.1 represents a halogen atom or a CH.sub.2CH.sub.2CH(CH.sub.3)CH.sub.2CH.sub.2OR group, and R represents a protecting group for a hydroxyl group, to form a 6-isopropenyl-3-methyl-9-decene compound (3) having a protected hydroxyl group at position 1: wherein R is as defined above; subjecting the 6-isopropenyl-3-methyl-9-decene compound (3) having the protected hydroxyl group at position 1 to a deprotection reaction to form 6-isopropenyl-3-methyl-9-decenol (4); and acetylating 6-isopropenyl-3-methyl-9-decenol (4) to form 6-isopropenyl-3-methyl-9-decenyl acetate (5).

##STR00001##

The present invention provides a process for preparing 6-isopropenyl-3-methyl-9-decenyl acetate (5): wherein Ac represents an acetyl group, the process comprising steps of: subjecting a 2-methyl-2,6-heptadiene compound (1) having a leaving group X at position 1: wherein X represents an acyloxy group having 1 to 10 carbon atoms including the carbon atom of the carbonyl group, an alkanesulfonyloxy group having 1 to 10 carbon atoms, an arenesulfonyloxy group having 6 to 20 carbon atoms, or a halogen atom, to a nucleophilic substitution reaction with a 3-methylpentyl nucleophilic reagent (2) having a protected hydroxyl group at position 5: wherein M represents Li, MgZ.sup.1, ZnZ.sup.1, Cu, CuZ.sup.1, or CuLiZ.sup.1, wherein Z.sup.1 represents a halogen atom or a CH.sub.2CH.sub.2CH(CH.sub.3)CH.sub.2CH.sub.2OR group, and R represents a protecting group for a hydroxyl group, to form a 6-isopropenyl-3-methyl-9-decene compound (3) having a protected hydroxyl group at position 1: wherein R is as defined above; subjecting the 6-isopropenyl-3-methyl-9-decene compound (3) having the protected hydroxyl group at position 1 to a deprotection reaction to form 6-isopropenyl-3-methyl-9-decenol (4); and acetylating 6-isopropenyl-3-methyl-9-decenol (4) to form 6-isopropenyl-3-methyl-9-decenyl acetate (5).

##STR00001##

Disclosed herein is a process for the conversion of polymers, oligomers, or mixtures thereof into shorter alkanes, carboxylic acids, alcohols, alkyl halides or aldehydes. This process includes contacting the polymers, oligomers, or mixtures thereof with the compound of formula (I):

Al(R.sup.1).sub.3  (I)

where R.sup.1 is independently selected at each occurrence thereof from the group consisting of H, aryl, C.sub.1-C.sub.8 alkyl, and C.sub.1-C.sub.8 alkoxy, as a reaction mixture, in the presence of a catalyst selected from the group consisting of a transition metal catalyst, a lanthanide series metal catalyst, or combinations thereof.

Disclosed herein is a process for the conversion of polymers, oligomers, or mixtures thereof into shorter alkanes, carboxylic acids, alcohols, alkyl halides or aldehydes. This process includes contacting the polymers, oligomers, or mixtures thereof with the compound of formula (I):

Al(R.sup.1).sub.3  (I)

where R.sup.1 is independently selected at each occurrence thereof from the group consisting of H, aryl, C.sub.1-C.sub.8 alkyl, and C.sub.1-C.sub.8 alkoxy, as a reaction mixture, in the presence of a catalyst selected from the group consisting of a transition metal catalyst, a lanthanide series metal catalyst, or combinations thereof.

The present invention provide for preparing a formylalkenyl alkoxymethyl ether compound of the following general formula (2): R.sup.3CH.sub.2OCH.sub.2O(CH.sub.2).sub.aCH═CHCHO (2), wherein R.sup.3 represents a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group; and “a” represents an integer of 1 to 10, the process comprising: hydrolyzing a dialkoxyalkenyl alkoxymethyl ether compound of the following general formula (1): R.sup.3CH.sub.2OCH.sub.2O(CH.sub.2).sub.aCH═CHCH(OR.sup.1)(OR.sup.2) (1), wherein R.sup.1 and R.sup.2 represent, independently of each other, a monovalent hydrocarbon group having 1 to 15 carbon atoms, or R.sup.1 and R.sup.2 may form together a divalent hydrocarbon group, R.sup.1-R.sup.2, having 2 to 10 carbon atoms; and R.sup.3 and “a” are as defined above, in the presence of an acid while removing an alcohol compound thus generated to form the formylalkenyl alkoxymethyl ether compound (2).

The present invention provide for preparing a formylalkenyl alkoxymethyl ether compound of the following general formula (2): R.sup.3CH.sub.2OCH.sub.2O(CH.sub.2).sub.aCH═CHCHO (2), wherein R.sup.3 represents a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group; and “a” represents an integer of 1 to 10, the process comprising: hydrolyzing a dialkoxyalkenyl alkoxymethyl ether compound of the following general formula (1): R.sup.3CH.sub.2OCH.sub.2O(CH.sub.2).sub.aCH═CHCH(OR.sup.1)(OR.sup.2) (1), wherein R.sup.1 and R.sup.2 represent, independently of each other, a monovalent hydrocarbon group having 1 to 15 carbon atoms, or R.sup.1 and R.sup.2 may form together a divalent hydrocarbon group, R.sup.1-R.sup.2, having 2 to 10 carbon atoms; and R.sup.3 and “a” are as defined above, in the presence of an acid while removing an alcohol compound thus generated to form the formylalkenyl alkoxymethyl ether compound (2).