A method for producing a homocyclic or heterocyclic compound includes reacting a compound of formula (I) with a compound of formula (II) in presence of a base:

##STR00001##

In formula (I), B is an unsaturated moiety selected from substituted or unsubstituted vinylene, ethynylene, aryleneethynylene, substituted or unsubstituted arylenevinylene, and a combination thereof, the vinylene or arylenevinylene has n (=0, 1 or 2) substituent(s) R.sup.2, G is an electron-withdrawing group, R.sup.1 is hydrogen or a substituent, and two of R.sup.1, R.sup.2 and G may joint together to form a ring. In formula (II), R.sup.3 and R.sup.4 are independently hydrogen or a substituent, R.sup.5 is an electron-withdrawing group, and two of R.sup.3, R.sup.4 and R.sup.5 may joint together to form a ring. The conjugate acid of the base has a pK.sub.a in the range of 1 to 15.

A method for producing a homocyclic or heterocyclic compound includes reacting a compound of formula (I) with a compound of formula (II) in presence of a base:

##STR00001##

In formula (I), B is an unsaturated moiety selected from substituted or unsubstituted vinylene, ethynylene, aryleneethynylene, substituted or unsubstituted arylenevinylene, and a combination thereof, the vinylene or arylenevinylene has n (=0, 1 or 2) substituent(s) R.sup.2, G is an electron-withdrawing group, R.sup.1 is hydrogen or a substituent, and two of R.sup.1, R.sup.2 and G may joint together to form a ring. In formula (II), R.sup.3 and R.sup.4 are independently hydrogen or a substituent, R.sup.5 is an electron-withdrawing group, and two of R.sup.3, R.sup.4 and R.sup.5 may joint together to form a ring. The conjugate acid of the base has a pK.sub.a in the range of 1 to 15.

New regulator compounds for a novel polymerization process for vinyl monomers, which yields polymers with improved control over composition and nearly full to full conservation of architectural integrity up to high conversion. The regulator compounds are defined by according to anyone of the Formulas 1A, 1B, 1C, 1D, 1E, 1F, 1G, 1H and 1I: ##STR00001## wherein R.sup.1 stands for an optionally substituted secondary or tertiary alkyl or secondary or tertiary aralkyl; Z.sup.1 stands for CN or a carboxylic acid ester of formula C(O)OR.sup.21; Z.sup.2 may be chosen from the group of CN, carboxylic acid, salts of carboxylic acids, carboxylic acid ester, carboxylic acid amides, (hetero)aryl, alkenyl and halogen; R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are each independently chosen from the group of H, alkyl, aralkyl, (hetero)aryl, CN and carboxylic acid ester of formula C(O)OR.sup.22; R.sup.7 stands for a primary alkyl or primary aralkyl, CN or hydrogen; Y stands for a bridging group and n is 2, 3, 4, 5 or 6; in case R.sup.1 stands for tertiary alkyl or tertiary aralkyl, R.sup.6 stands for a primary alkyl or primary aralkyl, CN or a carboxylic acid ester of formula C(O)OR.sup.26; in case R.sup.1 stands for a secondary alkyl or secondary aralkyl, R.sup.6 stands for a primary or secondary alkyl or primary or secondary aralkyl, CN, a carboxylic acid ester of formula C(O)OR.sup.26 or a phosphonic acid ester of formula P(O)(OR.sup.27).sub.2, a (hetero)aryl or an alkenyl; R.sup.21, R.sup.22, R.sup.26 and R.sup.27 each independently stand for alkyl or aralkyl having from 1-30 carbon atoms, optionally containing heteroatoms.

New regulator compounds for a novel polymerization process for vinyl monomers, which yields polymers with improved control over composition and nearly full to full conservation of architectural integrity up to high conversion. The regulator compounds are defined by according to anyone of the Formulas 1A, 1B, 1C, 1D, 1E, 1F, 1G, 1H and 1I: ##STR00001## wherein R.sup.1 stands for an optionally substituted secondary or tertiary alkyl or secondary or tertiary aralkyl; Z.sup.1 stands for CN or a carboxylic acid ester of formula C(O)OR.sup.21; Z.sup.2 may be chosen from the group of CN, carboxylic acid, salts of carboxylic acids, carboxylic acid ester, carboxylic acid amides, (hetero)aryl, alkenyl and halogen; R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are each independently chosen from the group of H, alkyl, aralkyl, (hetero)aryl, CN and carboxylic acid ester of formula C(O)OR.sup.22; R.sup.7 stands for a primary alkyl or primary aralkyl, CN or hydrogen; Y stands for a bridging group and n is 2, 3, 4, 5 or 6; in case R.sup.1 stands for tertiary alkyl or tertiary aralkyl, R.sup.6 stands for a primary alkyl or primary aralkyl, CN or a carboxylic acid ester of formula C(O)OR.sup.26; in case R.sup.1 stands for a secondary alkyl or secondary aralkyl, R.sup.6 stands for a primary or secondary alkyl or primary or secondary aralkyl, CN, a carboxylic acid ester of formula C(O)OR.sup.26 or a phosphonic acid ester of formula P(O)(OR.sup.27).sub.2, a (hetero)aryl or an alkenyl; R.sup.21, R.sup.22, R.sup.26 and R.sup.27 each independently stand for alkyl or aralkyl having from 1-30 carbon atoms, optionally containing heteroatoms.

The present invention provides a compound represented by formula (I) wherein symbols in the formula are as defined in the specification.

##STR00001##

The present invention provides a compound represented by formula (I) wherein symbols in the formula are as defined in the specification.

##STR00001##

This invention discloses the first example of palladium(II)-catalyzed -C(sp.sup.3)-H iodination or arylation of a wide range of ketones by using a commercially available aminooxyacetic acid auxiliary. This L, X-type directing group overcomes the limitation of the transient directing group approach for -C(sp.sup.3)-H functionalization of ketones. Practical advantages of this method include simple installation of the auxiliary without chromatography, exceptional tolerance of a-functional groups, double bonds and triple bonds and rapid access to diverse sterically hindered quaternary centers.

This invention discloses the first example of palladium(II)-catalyzed -C(sp.sup.3)-H iodination or arylation of a wide range of ketones by using a commercially available aminooxyacetic acid auxiliary. This L, X-type directing group overcomes the limitation of the transient directing group approach for -C(sp.sup.3)-H functionalization of ketones. Practical advantages of this method include simple installation of the auxiliary without chromatography, exceptional tolerance of a-functional groups, double bonds and triple bonds and rapid access to diverse sterically hindered quaternary centers.

A method for producing a homocyclic or heterocyclic compound includes reacting a compound of formula (I) with a compound of formula (II) in presence of a base:

##STR00001##

In formula (I), B is an unsaturated moiety selected from substituted or unsubstituted vinylene, ethynylene, aryleneethynylene, substituted or unsubstituted arylenevinylene, and a combination thereof, the vinylene or arylenevinylene has n (=0, 1 or 2) substituent(s) R.sup.2, G is an electron-withdrawing group, R.sup.1 is hydrogen or a substituent, and two of R.sup.1, R.sup.2 and G may joint together to form a ring. In formula (II), R.sup.3 and R.sup.4 are independently hydrogen or a substituent, R.sup.5 is an electron-withdrawing group, and two of R.sup.3, R.sup.4 and R.sup.5 may joint together to form a ring. The conjugate acid of the base has a pK.sub.a in the range of 1 to 15.

A method for producing a homocyclic or heterocyclic compound includes reacting a compound of formula (I) with a compound of formula (II) in presence of a base:

##STR00001##

In formula (I), B is an unsaturated moiety selected from substituted or unsubstituted vinylene, ethynylene, aryleneethynylene, substituted or unsubstituted arylenevinylene, and a combination thereof, the vinylene or arylenevinylene has n (=0, 1 or 2) substituent(s) R.sup.2, G is an electron-withdrawing group, R.sup.1 is hydrogen or a substituent, and two of R.sup.1, R.sup.2 and G may joint together to form a ring. In formula (II), R.sup.3 and R.sup.4 are independently hydrogen or a substituent, R.sup.5 is an electron-withdrawing group, and two of R.sup.3, R.sup.4 and R.sup.5 may joint together to form a ring. The conjugate acid of the base has a pK.sub.a in the range of 1 to 15.