The synthesis of inward-facing 3,6-di(2-pyridyl)pyridazine ligands
A new class of inward-facing bis(dpp-ligands) fused to rigid molecular racks are reported, eg 17 and 19. The 3,6-di(2-pyridyl)pyridazine ligand units are formed by the reaction of 3,6-di(2-pyridyl) s-tetrazine with molrac bis(olefins), eg 11 and 18 (followed by oxidation of the intermediate dihydrop...
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Published in: | Tetrahedron letters Vol. 37; no. 16; pp. 2825 - 2828 |
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Main Authors: | , , , |
Format: | Journal Article |
Language: | English |
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Elsevier Ltd
15-04-1996
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Abstract | A new class of inward-facing bis(dpp-ligands) fused to rigid molecular racks are reported, eg
17 and
19. The 3,6-di(2-pyridyl)pyridazine ligand units are formed by the reaction of 3,6-di(2-pyridyl)
s-tetrazine with molrac bis(olefins), eg
11 and
18 (followed by oxidation of the intermediate dihydropyridazines); additionally mono-olefin, mono-pyridazines
14 and
21 are reported. Molecular modelling and comments of the mechanism of product formation are included.
Rigid mono-and bis-DPP ligands are formed from molrac olefins with tetrazine
1 and DDQ. The steps in the conversion of
11 to
14 and of
14 to
17 are followed by
1H NMR. |
---|---|
AbstractList | A new class of inward-facing bis(dpp-ligands) fused to rigid molecular racks are reported, eg
17 and
19. The 3,6-di(2-pyridyl)pyridazine ligand units are formed by the reaction of 3,6-di(2-pyridyl)
s-tetrazine with molrac bis(olefins), eg
11 and
18 (followed by oxidation of the intermediate dihydropyridazines); additionally mono-olefin, mono-pyridazines
14 and
21 are reported. Molecular modelling and comments of the mechanism of product formation are included.
Rigid mono-and bis-DPP ligands are formed from molrac olefins with tetrazine
1 and DDQ. The steps in the conversion of
11 to
14 and of
14 to
17 are followed by
1H NMR. |
Author | Tepperman, Paul M. Butler, Douglas N. Warrener, Ronald N. Gau, Robert A. |
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Cites_doi | 10.1080/00397917508061439 10.1039/c39830001340 10.1016/S0040-4039(00)73484-8 10.1039/c39950001417 10.1021/ja00057a019 10.1016/S0040-4039(00)78363-8 10.1016/0040-4020(95)00569-T 10.1002/bscb.19921010702 10.1016/0040-4039(95)01164-D 10.1016/S0040-4039(00)61753-7 10.1021/ja00087a079 10.1071/CH9950241 |
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References | Sauer (BIB5) 1992; 101 Butler, Barrette, Snow (BIB7) 1975 Warrener, R. N.; Liu, L. Warrener, Abbenante, Kennard, Warrener, Abbenante, Solomon, Russell, Warrener, Elsey, Houghton, Warrener, Elsey, Pitt, Russell, Warrener, Pitt, Butler (BIB2) 1994; 116 Cioslowski, Sauer, Hetzenegger, Karcher, Hierstetter (BIB4) 1993; 115 Butler, Tepperman, Gau, Warrener, Watson, Kashyap (BIB9) 1995; 36 , Warrener, Elsey, Sankar, Butler, Pekos, Kennard (BIB3) 1994; 35 . Atkinson, Oliver, Paddon-Row (BIB8) 1993; 34 Voyer, Lamothe (BIB1) 1995; 51 Voyer (10.1016/0040-4039(96)00397-8_BIB1) 1995; 51 Warrener (10.1016/0040-4039(96)00397-8_BIB2_4) 1995; 48 Butler (10.1016/0040-4039(96)00397-8_BIB7) 1975 Sauer (10.1016/0040-4039(96)00397-8_BIB5) 1992; 101 Warrener (10.1016/0040-4039(96)00397-8_BIB3) 1994; 35 Warrener (10.1016/0040-4039(96)00397-8_BIB2_1) 1994; 116 Warrener (10.1016/0040-4039(96)00397-8_BIB2_5) 1983 Warrener (10.1016/0040-4039(96)00397-8_BIB2_2) 1994; 35 Butler (10.1016/0040-4039(96)00397-8_BIB9) 1995; 36 Atkinson (10.1016/0040-4039(96)00397-8_BIB8_1) 1993; 34 Cioslowski (10.1016/0040-4039(96)00397-8_BIB4) 1993; 115 Warrener (10.1016/0040-4039(96)00397-8_BIB2_3) 1995 10.1016/0040-4039(96)00397-8_BIB6 |
References_xml | – volume: 35 start-page: 6745 year: 1994 end-page: 6748 ident: BIB3 publication-title: Tetrahedron Lett. contributor: fullname: Kennard – volume: 51 start-page: 9241 year: 1995 end-page: 9284 ident: BIB1 publication-title: Tetrahedron contributor: fullname: Lamothe – volume: 34 start-page: 6147 year: 1993 end-page: 6150 ident: BIB8 publication-title: Tetrahedron Lett. contributor: fullname: Paddon-Row – start-page: 101 year: 1975 end-page: 106 ident: BIB7 publication-title: Syn. Commun. contributor: fullname: Snow – volume: 115 start-page: 1353 year: 1993 ident: BIB4 publication-title: J. Amer. Chem. Soc. contributor: fullname: Hierstetter – volume: 101 start-page: 521 year: 1992 end-page: 539 ident: BIB5 publication-title: Bull. Soc. Chim. Belg. contributor: fullname: Sauer – volume: 116 start-page: 3645 year: 1994 end-page: 3646 ident: BIB2 publication-title: J. Amer. Chem. Soc. contributor: fullname: Butler – volume: 36 start-page: 6145 year: 1995 end-page: 6148 ident: BIB9 publication-title: Tetrahedron Lett. contributor: fullname: Kashyap – start-page: 101 year: 1975 ident: 10.1016/0040-4039(96)00397-8_BIB7 publication-title: Syn. Commun. doi: 10.1080/00397917508061439 contributor: fullname: Butler – start-page: 1340 year: 1983 ident: 10.1016/0040-4039(96)00397-8_BIB2_5 publication-title: J. Chem. Soc., Chem. Commun. doi: 10.1039/c39830001340 contributor: fullname: Warrener – volume: 35 start-page: 6745 year: 1994 ident: 10.1016/0040-4039(96)00397-8_BIB3 publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(00)73484-8 contributor: fullname: Warrener – start-page: 1417 year: 1995 ident: 10.1016/0040-4039(96)00397-8_BIB2_3 publication-title: J. Chem. Soc., Chem. Commun. doi: 10.1039/c39950001417 contributor: fullname: Warrener – volume: 115 start-page: 1353 year: 1993 ident: 10.1016/0040-4039(96)00397-8_BIB4 publication-title: J. Amer. Chem. Soc. doi: 10.1021/ja00057a019 contributor: fullname: Cioslowski – volume: 35 start-page: 7639 year: 1994 ident: 10.1016/0040-4039(96)00397-8_BIB2_2 publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(00)78363-8 contributor: fullname: Warrener – volume: 51 start-page: 9241 year: 1995 ident: 10.1016/0040-4039(96)00397-8_BIB1 publication-title: Tetrahedron doi: 10.1016/0040-4020(95)00569-T contributor: fullname: Voyer – volume: 101 start-page: 521 year: 1992 ident: 10.1016/0040-4039(96)00397-8_BIB5 publication-title: Bull. Soc. Chim. Belg. doi: 10.1002/bscb.19921010702 contributor: fullname: Sauer – volume: 36 start-page: 6145 year: 1995 ident: 10.1016/0040-4039(96)00397-8_BIB9 publication-title: Tetrahedron Lett. doi: 10.1016/0040-4039(95)01164-D contributor: fullname: Butler – ident: 10.1016/0040-4039(96)00397-8_BIB6 – volume: 34 start-page: 6147 year: 1993 ident: 10.1016/0040-4039(96)00397-8_BIB8_1 publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(00)61753-7 contributor: fullname: Atkinson – volume: 116 start-page: 3645 year: 1994 ident: 10.1016/0040-4039(96)00397-8_BIB2_1 publication-title: J. Amer. Chem. Soc. doi: 10.1021/ja00087a079 contributor: fullname: Warrener – volume: 48 start-page: 241 year: 1995 ident: 10.1016/0040-4039(96)00397-8_BIB2_4 publication-title: Aust. J. Chem. doi: 10.1071/CH9950241 contributor: fullname: Warrener |
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Snippet | A new class of inward-facing bis(dpp-ligands) fused to rigid molecular racks are reported, eg
17 and
19. The 3,6-di(2-pyridyl)pyridazine ligand units are... |
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Title | The synthesis of inward-facing 3,6-di(2-pyridyl)pyridazine ligands |
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