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Angewandte Chemie International Edition in English

Volumn 20, Issue 3, 1981, Pages 263-265

Cyclization of a Seco‐porphyrinogen to Nickel(II) C,D‐Tetradehydrocorrinates

(3) Angst, Christof a Kratky, Christoph b Eschenmoser, Albert a

a ETH ZURICH (Switzerland)

b Universitat (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84985502364 PISSN: 05700833 EISSN: 15213773 Source Type: Journal
DOI: 10.1002/anie.198102631 Document Type: Article

Times cited : (22)

References (28)

1
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- 1,2,3,7,8,20-Hexahydroporphyrin, ein sich leicht bildendes, zu Porphyrinogen isomeres Ligandsystem
- (1980) Angewandte Chemie , vol.92 , pp. 141
- Johansen, J.E.¹ Angst, Ch.² Kratky, Ch.³ Eschfnmoser, A.⁴

2
- 84985531895
- (1980) Angew. Chem. Int. Ed. Engl. , vol.19 , pp. 141

3
- 84985632156
- B. J. Zagalak, W. Friedrich, de Gruytcr, Berlin
- (1979) 12 and Intrinsic Factor (Proc. 3rd Ear. Symp. Zürich) , pp. 89
- Eschenmoser, A.¹

4
- 84985627587
- Dissertation. ETH Zürich (Prom. No. 6783) 1981 (in press)
- Angst, Ch.¹

5
- 0004690018
- Gegenseitige Umwandlung der Chromophorsysteme des Porphyrinogens und 2,3,7,8,12,13-Hexahydroporphyrins
- (1981) Angewandte Chemie , vol.93 , pp. 273
- Johansen, J.E.¹ Piermartit, V.² Angst, Ch.³ Diener, E.⁴ Kratky, Ch.⁵ Eschenmoser, A.⁶

6
- 84985521971
- (1981) Angew. Chem. Int. Ed. Engl. , vol.20 , pp. 261

7
- 0017413246
- (A→D)-Ringschluß eines Nickel(II)-Δ18-dehydro-1-methyliden-1,19-secocorrinats
- (1977) Angewandte Chemie , vol.89 , pp. 475
- Ra‐setti, V.¹ Kräutler, B.² Pfaltz, A.³ Eschenmoser, A.⁴

8
- 84980149265
- resp.
- (1977) Angew. Chem. Int. Ed. Engl. , vol.16 , pp. 459

9
- 49549143451
- cf. also
- (1975) Tetrahedron , vol.31 , pp. 2639
- Scott, A.I.¹

10
- 84985626775
- This type of ligand was first observed in our laboratory by S. Ofner during work on a synthesis of isobacteriochlorins. A de novo synthesis of metal‐free C, D‐tetradchydrocorrins will be published later, cf., Dissertation, ETH Zürich
- (1981)
- Ofner, S.¹

11
- 37049112959
- and literature cited therein
- (1980) Chem. Soc. Rev. , vol.9 , pp. 125
- Johnson, A.W.¹

12
- 84981413555
- J. Chem. Soc. C , vol.1966 , pp. 30
- Dolphin, D.¹ Harris, R.L.N.² Huppalz, J.L.³ Johnson, A.W.⁴ Kay, I.T.⁵

13
- 0005962945
- C 1971
- J. Chem. Soc. C , pp. 536
- Dicker, D.¹ Crigg, R.² Johnson, A.W.³ Pinnock, H.⁴ Richardson, K.⁵ van den Brock, P.⁶

14
- 0542422652
- F : nomenclature, see, D. Dolphin, Academic Press, New York
- (1978) The Porphyrins , vol.1 , pp. 1-27
- Bonnetl, R.¹

15
- 84985577760
- 2251
- (1979) Pure Appl. Chem. , vol.51
- Merrill, J.E.¹ Loening, K.L.²

16
- 84917844898
- 4, in 80% methanol (yield 51%). For the synthesis of the starting material, a modified procedure of that described by
- (1979) Zh. Org. Khim. , vol.15 , pp. 1086
- Mironov, A.F.¹ Popova, O.D.² Alarkon³ Bairamov, K.M.⁴ Evsligneeva, R.P.⁵

17
- 84985514010
- was used. For details, cf. [tc]
- (1979) J. Org. Chem. USSR , vol.15 , pp. 970

18
- 84985544144
- (a) HPLC: Partisil 5; penlane‐dimethoxyethane‐triethylamine 200:2:1

19
- 84985544140
- (b) present to 21% in the mixture of diastereomers (6)

20
- 84985542497
- (a) Identified by comparison of UV/VIS and mass spectra with those of 9 [7b]; this compound was prepared [1c] from nonamethyl‐10, 23‐dihydrobilin dihydrobromide by Johnton‐cyclization [3b]

21
- 84916305710
- J. Chem. Soc. C , vol.1967 , pp. 1648
- Clarke, D.A.¹ Crigg, R.² Harris, R.L.N.³ Johnson, A.W.⁴ Kay, I.T.⁵ Shelton, K.W.⁶

22
- 84985530937
- max = 303 nm (lgr = 4.25). 399(4.33), 455 (4.03). 508 (3.87), 675 (3.90).

23
- 84985608343
- (a) We thank Dr. R. Schwesinger for a sample of TBD; cf. also [1d], reference [4]

24
- 84985608353
- Schwevsinger, R.¹

25
- 84985581101
- 11‐1.2, 3.7.8, 12.13.17.18‐nonamethyl (!)‐1, 7, 8, 20‐tetrahydroporphyrinate; for details cf. [1c].

26
- 84985544152
- 2O, benzene, anaerobic, 2.5 h, 60°C. diastereomers of types 11 and 6 are formed, yields ca. 15 and 12%, respectively (cf. [1c]).

27
- 84955881744
- Konformationelle Kopplung zwischen Ring A und Ring B in Isobakteriochlorinen
- (1981) Angewandte Chemie , vol.93 , pp. 204
- Kralky, Ch.¹ Angst, Ch.² Johansen, J.E.³

28
- 84985581037
- (1981) Angew. Chem. Int. Ed. Engl. , vol.20 , pp. 211

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