What is claimed is:
1. A method of making an oxochlorin, comprising the steps of:
oxidizing a chlorin to produce a mixture of hydroxychlorin and oxochlorin; and then
oxidizing said hydroxychlorin in said mixture with DDQ to produce a mixture consisting essentially of oxochlorin.
2. The method according to claim 1, wherein said step of oxidizing a chlorin is carried out by exposing said chlorin to alumina.
3. The method according to claim 1, wherein said step of oxidizing a chlorin is carried out in the presence of an oxidizing agent.
4. The method according to claim 3, wherein said oxidizing agent is oxygen or air.
5. The method according to claim 1, wherein said step of oxidizing a chlorin is carried out at a temperature of from 0 to 100 C.
6. The method according to claim 1, wherein said step of oxidizing a chlorin is carried out in an aromatic organic solvent.
7. The method according to claim 1, wherein said step of oxidizing a chlorin is carried out in toluene.
8. The method according to claim 1, wherein said step of oxidizing said hydroxychlorin is carried out at a temperature of from 0 to 100 C.
9. The method according to claim 1, wherein said step of oxidizing said hydroxychlorin is carried out in an aromatic organic solvent.
10. The method according to claim 1, wherein said step of oxidizing said hydroxychlorin is carried out in toluene.
11. The method according to claim 1, wherein said oxochlorin is a C-methylated chlorin.
12. The method according to claim 1, wherein said chlorin is metalated.
13. A method of making an oxochlorin, comprising the steps of:
(a) providing a chlorin of Formula X:
13
wherein:
M is a metal selected from the group consisting of Zn, Mg, Pt, Pd. Sn and Al, or M is absent;
K1, K2, K3, and K4 are hetero atoms independently selected from the group consisting of N, O, S, Se, Te, and CH;
S1, S2, S3, S4, S5, S6, S7, S8, S9, S10, S11, S12, S13, and S14 are independently selected from the group consisting of H, aryl, phenyl, alkyl, cycloalkyl, spiroalkyl, alkenyl, alkynyl, halogen, alkoxy, alkylthio, perfluoroalkyl, perfluoroaryl, pyridyl, cyano, thiocyanato, nitro, amino, alkylamino, acyl, sulfoxyl, sulfonyl, imido, amido, and carbamoyl;
and optionally either S1 and S5 are trans-substituted linking groups Q1 and Q2, S2 and S6 are trans-substituted linking groups Q1 and Q2, S10 and S12 are trans-substituted linking groups Q1 and Q2, or S9 and S11 are trans-substituted linking groups Q1 and Q2; and
Q1 and Q2 are independently selected linking groups of the formula:
R1R2nR3Y
wherein:
n is from 0 or 1 to 5 or 10;
R3 may be present or absent;
R1, R2, and R3 are each independently selected from the group consisting of ethene, ethyne, aryl, and heteroaryl groups, which aryl and heteroaryl groups may be unsubstituted or substituted one or more times with H, aryl, phenyl, cycloalkyl, alkyl, alkenyl, alkynyl, halogen, alkoxy, alkylthio, perfluoroalkyl, perfluoroaryl, pyridyl, cyano, thiocyanato, nitro, amino, alkylamino, acyl, sulfoxyl, sulfonyl, imido, amido, and carbamoyl;
Y is a protected or unprotected reactive substituent selected from the group consisting of hydroxy, thio, seleno, telluro, ester, carboxylic acid, boronic acid, phenol, silane, sulfonic acid, phosphonic acid, alkylthiol, formyl, halo, alkenyl, alkynyl, haloalkyl, dialkyl phosphonate, alkyl sulfonate, alkyl carboxylate, acetylacetone, and dialkyl boronate groups;
(b) oxidizing said chlorin to produce a mixture of hydroxychlorin and oxochlorin; and then
(c) oxidizing said hydroxychlorin in said mixture with DDQ in toluene to produce a mixture consisting essentially of oxochlorin, said oxochlorin comprising a compound of Formula X where S7 and S13 are togetherO.
14. The method according to claim 13, wherein neither S8 nor S14 is H.
15. The method according to claim 13, wherein S9 and S11 are trans-substituted linking groups Q1 and Q2.
16. The method according to claim 13, wherein S10 and S12 are trans-substituted linking groups Q1 and Q2.
17. The method according to claim 13, wherein M is present.
18. The method according to claim 13, wherein M is Zn or Mg.
19. The method according to claim 13, wherein M is absent.
20. The method according to claim 13, wherein K1, K2, K3, and K4 are independently selected from the group consisting of N, O, S, and CH.
21. The method according to claim 13, wherein K1, K2, K3, and K4 are all N.
22. The method according to claim 13, wherein S4, S7, S8, S9, S10, S11, S12, S13, and S14 are all alkyl.
23. A trans substituted oxochlorin compound of Formula X:
14
wherein:
M is a metal selected from the group consisting of Zn, Mg, Pt, Pd. Sn and Al, or M is absent;
K1, K2, K3, and K4 are hetero atoms independently selected from the group consisting of N, O, S, Se, Te, and CH;
S1, S2, S3, S4, S5, S6 , S8, S9, S10, S11, S12, and S14 are independently selected from the group consisting of H, aryl, phenyl, alkyl, cycloalkyl, spiroalkyl, alkenyl, alkynyl, halogen, alkoxy, alkylthio, perfluoroalkyl, perfluoroaryl, pyridyl, cyano, thiocyanato, nitro, amino, alkylamino, acyl, sulfoxyl, sulfonyl, imido, amido, and carbamoyl;
wherein S7 and S13 are togetherO;
and either S1 and S5 are trans-substituted linking groups Q1 and Q2, S10 and S12 are trans-substituted linking groups Q1 and Q2, S9 and S11 are trans-substituted linking groups Q1 and Q2, or S9 and S11 are trans-substituted linking groups Q1 and Q2; and
Q1 and Q2 are independently selected linking groups of the formula:
R1R2nR3Y
wherein:
n is from 0 or 1 to 5 or 10;
R3 may be present or absent;
R1, R2, and R3 are each independently selected from the group consisting of ethene, ethyne, aryl, and heteroaryl groups, which aryl and heteroaryl groups may be unsubstituted or substituted one or more times with H, aryl, phenyl, cycloalkyl, alkyl, alkenyl, alkynyl, halogen, alkoxy, alkylthio, perfluoroalkyl, perfluoroaryl, pyridyl, cyano, thiocyanato, nitro, amino, alkylamino, acyl, sulfoxyl, sulfonyl, imido, amido, and carbamoyl; and
Y is a protected or unprotected reactive substituent selected from the group consisting of hydroxy, thio, seleno, telluro, ester, carboxylic acid, boronic acid, phenol, silane, sulfonic acid, phosphonic acid, alkylthiol, formyl, halo, alkenyl, alkynyl, haloalkyl, dialkyl phosphonate, alkyl sulfonate, alkyl carboxylate, acetylacetone, and dialkyl boronate groups.
24. The compound according to claim 23, wherein S9 and S11 are trans-substituted linking groups Q1 and Q2.
25. The compound according to claim 23, wherein S10 and S12 are trans-substituted linking groups Q1 and Q2.
26. The compound according to claim 23, wherein neither S8 nor S14 is H.
27. The compound according to claim 23, wherein M is present.
28. The compound according to claim 23, wherein M is Zn or Mg.
29. The compound according to claim 23, wherein M is absent.
30. The compound according to claim 23, wherein K1, K2, K3, and K4 are independently selected from the group consisting of N, O, S, and CH.
31. The compound according to claim 23, wherein K1, K2, K3, and K4 are all N.
32. The compound according to claim 23, wherein S4, S7, S8, S9, S10, S11, S12, S13, and S14 are all alkyl.
The claims below are in addition to those above.
All refrences to claim(s) which appear below refer to the numbering after this setence.
1. An apparatus for seaming a peripheral curl of a can end onto a flange of a can body, said can end having a wall extending radially inward from said peripheral curl and inclined between about 20\xb0 and about 60\xb0 with respect to a central axis of said can end, comprising:
a) a chuck for locating within said can end, said chuck comprising upper and lower circumferentially extending walls forming a juncture therebetween, said lower wall inclined away from said upper wall so as to form a driving surface between said upper and lower walls, said driving surface subtending an angle of between about 120\xb0 and 150\xb0, said upper wall being substantially cylindrical; and
b) at least one seaming roll adapted to urge an upper portion of said inclined wall of said can end against said upper wall of said chuck so as to deform said peripheral curl and said flange into a seam joining said can end to said can body.
2. The apparatus according to claim 1, wherein said substantially cylindrical wall is inclined with respect to said central axis by not more than about 4\xb0 such that said driving surface subtends an angle of between 116\xb0 and 154\xb0.
3. The apparatus according to claim 1, wherein said driving surface subtends an angle of between about 130\xb0 and 150\xb0.
4. The apparatus according to claim 3, wherein said driving surface subtends an angle of between about 135\xb0 and 140\xb0.
5. An apparatus for seaming a can end onto a flange of a can body, said can end having a circumferentially extending peripheral curl and a wall extending circumferentially and radially inward from said curl and an annular reinforcing bead extending radially inward from said wall, said reinforcing bead having an interior surface, said peripheral curl comprising a seaming panel and a radiused portion extending from said seaming panel to said wall, comprising:
a) a chuck for locating within said can end, said chuck comprising (i) upper and lower circumferentially extending walls forming a juncture therebetween, said lower wall inclined away from said upper wall so as to form a driving surface therebetween, said driving surface subtending an angle of between about 120\xb0 and 150\xb0, said upper wall being substantially cylindrical, and (ii) a downwardly extending annular bead, said chuck annular bead sized and located so as not to contact said interior surface of said can end annular reinforcing bead when said chuck is located within said can end; and
b) at least one seaming roll adapted to urge an upper portion of said inclined wall of said can end against said upper wall of said chuck so as to deform said peripheral curl and said flange into a seam joining said can end to said can body.
6. The apparatus according to claim 5, wherein said substantially cylindrical wall is inclined with respect to said central axis by not more than about 4\xb0 such that said driving surface subtends an angle of between 116\xb0 and 154\xb0.
7. The apparatus according to claim 5, wherein said driving surface subtends an angle of between about 130\xb0 and 150\xb0.
8. The apparatus according to claim 7, said driving surface subtends an angle of between about 135\xb0 and 140\xb0.
9. The apparatus according to claim 5, wherein said lower wall of said chuck is adapted to drive rotation of said can end and said can body while said chuck is located within said can end.
10. The apparatus according to claim 5, wherein said juncture between said upper and lower walls of said chuck is adapted to drive rotation of said can end and said can body while said chuck is located within said can end.
11. An apparatus for seaming a peripheral curl of a can end onto a flange of a can body, said can end having a wall extending radially inward from said peripheral curl, comprising:
a) a chuck adapted to be located within said can end, said chuck comprising upper and lower circumferentially extending surfaces forming a juncture therebetween, said upper surface being substantially cylindrical, said lower surface extending inwardly and downwardly from said upper surface to an end point of said lower surface such that a line between the juncture and the end point of the lower surface is inclined between about 30\xb0 and about 60\xb0 with respect to a central axis of said chuck; and
b) at least one seaming roll adapted to urge an upper portion of said wall of said can end against said upper surface of said chuck so as to deform said peripheral curl and said flange into a seam joining said can end to said can body.
12. The apparatus according to claim 11, wherein said line between the juncture and the end point of the lower surface is inclined between about 30\xb0 and about 50\xb0 with respect to said central axis of said chuck.
13. The apparatus according to claim 11, wherein said line between the juncture and the end point of the lower surface is inclined between about 40\xb0 to about 45\xb0 with respect to said central axis of said chuck.
14. The apparatus according to claim 11, wherein said lower surface between the juncture and the end point of the lower surface is straight.
15. The apparatus according to claim 11, wherein said chuck lower surface between the juncture and the end point of the lower surface forms a frustum of a right circular cone.
16. The apparatus according to claim 11, wherein said chuck further comprises a bead extending from said end point of said lower surface.
17. The apparatus according to claim 16, wherein said bead is circumferential.
18. The apparatus according to claim 16, wherein said bead does not have driving contact with a concave surface of a reinforcing bead of the end during seaming.
19. The apparatus according to claim 16, wherein said bead has an arcuate shape in cross section.
20. The apparatus according to claim 19, wherein an outer portion of said arcuate shape of said bead extends directly from the end point of the lower surface.
21. The apparatus according to claim 11, wherein said substantially cylindrical surface is inclined with respect to said central axis by not more than about 4\xb0.
22. The apparatus according to claim 11, wherein said juncture between said upper and lower surfaces of said chuck forms a driving surface for contacting the end during seaming.
23. The apparatus according to claim 22, wherein said chuck between said juncture and said end point of the lower surface forms another driving surface for contacting the end during seaming.