Provided is a method with which an α-allylated cycloalkanone is obtained from a macroyclic compound used as a starting material. The method is a method for producing an α-allylated cycloalkanone represented by General Formula (IV), and the method includes a step of reacting a compound represented by General Formula (I) and/or a compound represented by General Formula (II) with a compound represented by General Formula (III) in the presence of an acid catalyst to produce an α-allylated cycloalkanone represented by General Formula (IV), the acid catalyst including an acid catalyst that includes an ammonium cation and an anion. ##STR00001##
where R.sup.1, R.sup.2, and R.sup.3 are the same or different and each of them is an alky group having 1 or mom and 4 or less of carbon atoms, the group -A.sup.1- (it should be noted that the front bond refers to a bond that binds to the carbon atom C.sup.1 and the back bond refers to a bond that binds to the carbon atom C.sup.2) is an alkylene group having 4 or more and 20 or les of carbon atoms that optionally contains a hetero atom and optionally has a substituent, and R.sup.4 is a hydrogen atom or an alkyl group having 1 or more and 4 or less of carbon atoms.

Solid base catalysts and their use for the base-catalyzed depolymerization (BCD) of lignin to compounds such as aromatics are presented herein. Exemplary catalysts include layered double hydroxides (LDHs) as recyclable, heterogeneous catalysts for BCD of lignin.

The present invention refers to a process for preparing a compound of formula (I) or a pharmaceutically acceptable salt thereof: wherein R is (C.sub.3-C.sub.10)alkyl, or ω-trifluoro(C.sub.3-C.sub.10)alkyl; R.sub.1 and R.sub.2 are, independently, hydrogen, hydroxy, (C.sub.1-C.sub.8) alkoxy, (C.sub.1-C.sub.8) alkylthio, halo, trifluoromethyl or 2,2,2-trifluoroethyl; or one of R.sub.1 and R.sub.2 is in ortho position to the R—O— group and, taken together with the same R—O—, represents a Formula (A) group where R.sub.0 is (C.sub.2-C.sub.9)alkyl; R.sub.3 and R.sub.4 are, independently, hydrogen, (C.sub.1-C.sub.4)alkyl; or R.sub.4 is hydrogen and R.sub.5 is a group selected from —CH.sub.2—OH, —CH.sub.2—O—(C.sub.1-C.sub.6)alkyl, —CH(CH.sub.3)—OH, —(CH.sub.2).sub.2—S—CH.sub.3, benzyl and 4-hydroxybenzyl; or R.sub.4 and R.sub.5, taken together with the adjacent carbon atom, form a (C.sub.3-C.sub.6)cycloalkyl residue; R.sub.5 and R.sub.6 are independently hydrogen or (C.sub.1-C.sub.6)alkyl; or taken together with the adjacent nitrogen atom form a 5-6 membered monocyclic saturated heterocycle, optionally containing one additional heteroatom chosen among —O—, —S— and —NR.sub.7— where R.sub.7 is hydrogen or (C.sub.1-C.sub.6) alkyl; and wherein optionally one or more hydrogen atom in the groups R, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6, preferably in the R group, can be substituted by a deuterium atom.

##STR00001##

The present invention refers to a process for preparing a compound of formula (I) or a pharmaceutically acceptable salt thereof: wherein R is (C.sub.3-C.sub.10)alkyl, or ω-trifluoro(C.sub.3-C.sub.10)alkyl; R.sub.1 and R.sub.2 are, independently, hydrogen, hydroxy, (C.sub.1-C.sub.8) alkoxy, (C.sub.1-C.sub.8) alkylthio, halo, trifluoromethyl or 2,2,2-trifluoroethyl; or one of R.sub.1 and R.sub.2 is in ortho position to the R—O— group and, taken together with the same R—O—, represents a Formula (A) group where R.sub.0 is (C.sub.2-C.sub.9)alkyl; R.sub.3 and R.sub.4 are, independently, hydrogen, (C.sub.1-C.sub.4)alkyl; or R.sub.4 is hydrogen and R.sub.5 is a group selected from —CH.sub.2—OH, —CH.sub.2—O—(C.sub.1-C.sub.6)alkyl, —CH(CH.sub.3)—OH, —(CH.sub.2).sub.2—S—CH.sub.3, benzyl and 4-hydroxybenzyl; or R.sub.4 and R.sub.5, taken together with the adjacent carbon atom, form a (C.sub.3-C.sub.6)cycloalkyl residue; R.sub.5 and R.sub.6 are independently hydrogen or (C.sub.1-C.sub.6)alkyl; or taken together with the adjacent nitrogen atom form a 5-6 membered monocyclic saturated heterocycle, optionally containing one additional heteroatom chosen among —O—, —S— and —NR.sub.7— where R.sub.7 is hydrogen or (C.sub.1-C.sub.6) alkyl; and wherein optionally one or more hydrogen atom in the groups R, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6, preferably in the R group, can be substituted by a deuterium atom.

##STR00001##

Provided is a method with which an α-allylated cycloalkanone is obtained from a macroyclic compound used as a starting material. The method is a method for producing an α-allylated cycloalkanone represented by General Formula (IV), and the method includes a step of reacting a compound represented by General Formula (I) and/or a compound represented by General Formula (II) with a compound represented by General Formula (III) in the presence of an acid catalyst to produce an α-allylated cycloalkanone represented by General Formula (IV), the acid catalyst including an acid catalyst that includes an ammonium cation and an anion.

##STR00001##

where R.sup.1, R.sup.2, and R.sup.3 are the same or different and each of them is an alky group having 1 or mom and 4 or less of carbon atoms, the group -A.sup.1- (it should be noted that the front bond refers to a bond that binds to the carbon atom C.sup.1 and the back bond refers to a bond that binds to the carbon atom C.sup.2) is an alkylene group having 4 or more and 20 or les of carbon atoms that optionally contains a hetero atom and optionally has a substituent, and R.sup.4 is a hydrogen atom or an alkyl group having 1 or more and 4 or less of carbon atoms.

Provided is a method with which an α-allylated cycloalkanone is obtained from a macroyclic compound used as a starting material. The method is a method for producing an α-allylated cycloalkanone represented by General Formula (IV), and the method includes a step of reacting a compound represented by General Formula (I) and/or a compound represented by General Formula (II) with a compound represented by General Formula (III) in the presence of an acid catalyst to produce an α-allylated cycloalkanone represented by General Formula (IV), the acid catalyst including an acid catalyst that includes an ammonium cation and an anion.

##STR00001##

where R.sup.1, R.sup.2, and R.sup.3 are the same or different and each of them is an alky group having 1 or mom and 4 or less of carbon atoms, the group -A.sup.1- (it should be noted that the front bond refers to a bond that binds to the carbon atom C.sup.1 and the back bond refers to a bond that binds to the carbon atom C.sup.2) is an alkylene group having 4 or more and 20 or les of carbon atoms that optionally contains a hetero atom and optionally has a substituent, and R.sup.4 is a hydrogen atom or an alkyl group having 1 or more and 4 or less of carbon atoms.

Provided is a method with which an α-allylated cycloalkanone is obtained from a cyclic compound cycloalkanone used as a starting material. The method is a method for producing an α-allylated cycloalkanone represented by General Formula (III), and the method includes: a step 1: reacting a compound represented by General Formula (I) and alcohol having 1 or more and 4 or less of carbon atoms in the presence of a first acid catalyst and optionally a dehydrating agent; and a step 2: reacting a crude product obtained in the step 1 and a compound represented by General Formula (II) in the presence of a second acid catalyst to produce an α-allylated cycloalkanone represented by General Formula (III). The step 1 and the step 2 are consecutively performed. In the formulae above, the group -A.sup.1- (it should be noted that the front bond refers to a bond that binds to the carbon atom C.sup.1 and the back bond refers to a bond that binds to the carbon atom C.sup.2) is an alkylene group having 4 or more and 20 or less of carbon atoms that optionally contains a hetero atom and optionally has a substituent, and R.sup.4 is a hydrogen atom or an alkyl group having 1 or more and 4 or less of carbon atoms.

Provided is a method with which an α-allylated cycloalkanone is obtained from a cyclic compound cycloalkanone used as a starting material. The method is a method for producing an α-allylated cycloalkanone represented by General Formula (III), and the method includes: a step 1: reacting a compound represented by General Formula (I) and alcohol having 1 or more and 4 or less of carbon atoms in the presence of a first acid catalyst and optionally a dehydrating agent; and a step 2: reacting a crude product obtained in the step 1 and a compound represented by General Formula (II) in the presence of a second acid catalyst to produce an α-allylated cycloalkanone represented by General Formula (III). The step 1 and the step 2 are consecutively performed. In the formulae above, the group -A.sup.1- (it should be noted that the front bond refers to a bond that binds to the carbon atom C.sup.1 and the back bond refers to a bond that binds to the carbon atom C.sup.2) is an alkylene group having 4 or more and 20 or less of carbon atoms that optionally contains a hetero atom and optionally has a substituent, and R.sup.4 is a hydrogen atom or an alkyl group having 1 or more and 4 or less of carbon atoms.

Disclosed herein is an efficient, environment friendly and commercially viable process for preparation of chloromethylated compound of formula I in substantially pure form and high yield, from the compound of formula II. The process includes contacting the compound of formula II with a chloromethylating agent generated in-situ by reaction of a formaldehyde precursor and hydrogen chloride, in a suitable solvent/contacting medium and in the presence of a catalytic amount of a short chain/low molecular weight carboxylic acid of formula III. I II III wherein, R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are as defined in the description. ##STR00001##

A method is provided for using twisted acenes, and more particularly to configurationally stable twisted acenes that are imbedded into the structure of [7]helicene at the fulcrum ring to form useable material structures. The helicene propagates its chiral nature into the acene, while acting as a locking mechanism to thermal racemization. These doubly-helical compounds are part of a new homologous series of polycyclic aromatic hydrocarbons, namely the [7]helitwistacenes. Such [7]helitwistacenes have utility as materials suitable for forming a circularly polarized organic light emitting diode (CP-OLED) for direct emission of circularly polarized (CP) light for the fabrication of high efficiency electronic displays.