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Various thiaza[2.2]metacyclophanes including synthetic procedures: [17a] P. Knops, P.-M. Windscheif, F. Vögtle, A. Roloff, M. Jansen, M. Nieger, E. Niecke, Y. Okamoto, Chem. Ber. 1991, 124, 1585-1590. [17b] D. Müller, M. Böhme, M. Nieger, K. Rissanen, F. Vögtle, J. Chem. Soc., Perkin Trans, 1, 1996, 2937-2943. - For helically chiral [2.2]metacyclophanes see also [17c] [2.2](1,3)Cyclophan-1-one: K. Mislow, M. Brzechffa, H. W. Gschwend, R. T. Puckett, J. Am. Chem. Soc. 1973, 95, 621-622. - For [2.2]metacyclophan-1-ene see also [17d] H. Blaschke, V. Boekelheide, J. Am. Chem. Soc. 1967, 89, 2747-2748. [17e] D. Taylor, Austr. J. Chem. 1978, 31, 1235
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Various thiaza[2.2]metacyclophanes including synthetic procedures: [17a] P. Knops, P.-M. Windscheif, F. Vögtle, A. Roloff, M. Jansen, M. Nieger, E. Niecke, Y. Okamoto, Chem. Ber. 1991, 124, 1585-1590. [17b] D. Müller, M. Böhme, M. Nieger, K. Rissanen, F. Vögtle, J. Chem. Soc., Perkin Trans, 1, 1996, 2937-2943. - For helically chiral [2.2]metacyclophanes see also [17c] [2.2](1,3)Cyclophan-1-one: K. Mislow, M. Brzechffa, H. W. Gschwend, R. T. Puckett, J. Am. Chem. Soc. 1973, 95, 621-622. - For [2.2]metacyclophan-1-ene see also [17d] H. Blaschke, V. Boekelheide, J. Am. Chem. Soc. 1967, 89, 2747-2748. [17e] D. Taylor, Austr. J. Chem. 1978, 31, 1235
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3042885235
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[2.2](1,3)Cyclophan-1-one
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3042916711
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Various thiaza[2.2]metacyclophanes including synthetic procedures: [17a] P. Knops, P.-M. Windscheif, F. Vögtle, A. Roloff, M. Jansen, M. Nieger, E. Niecke, Y. Okamoto, Chem. Ber. 1991, 124, 1585-1590. [17b] D. Müller, M. Böhme, M. Nieger, K. Rissanen, F. Vögtle, J. Chem. Soc., Perkin Trans, 1, 1996, 2937-2943. - For helically chiral [2.2]metacyclophanes see also [17c] [2.2](1,3)Cyclophan-1-one: K. Mislow, M. Brzechffa, H. W. Gschwend, R. T. Puckett, J. Am. Chem. Soc. 1973, 95, 621-622. - For [2.2]metacyclophan-1-ene see also [17d] H. Blaschke, V. Boekelheide, J. Am. Chem. Soc. 1967, 89, 2747-2748. [17e] D. Taylor, Austr. J. Chem. 1978, 31, 1235
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The yields of the unstable cyclophane 15a are low (approx. 0.5%)
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[27a] The yields of the unstable cyclophane 15a are low (approx. 0.5%): M. Habel, F. Vögtle, M. Nieger, Eur. J. Org. Chem. 1998, 1471-1477.
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3042911478
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note
-
The deformation angles α and α' of 15b at the HF-SCF/WDZ level are 5.3-5.4 and 12.3 -14.6°, respectively, which should be compared to the values of [2.2]metacyclophane being 4.3 and 12.2°. The non-bonded C8-C16 distances in both compounds are calculated to be 2.64 and 2.69 Å.
-
-
-
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111
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3042988390
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note
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Low yields were observed in syntheses of 16 using appropriate N-tosylated or triflated phenol building blocks. The cyclophanes 16a, b were detected by GC-MS but isolation and complete characterisation failed so far.
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112
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3042914017
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[34b] Non chiral dithiacyclophanes: L.W. Jenneskens, F. J. J. de Kanter, P. A. Kraakman, L. A. M. Turkenburg, W. E. Koolhaas, W. H. de Wolf, F. Bickelhaupt, Y. Tobe, K. Kakiuchi, Y. Odaira, J. Am. Chem. Soc. 1985, 107, 3716-3718.
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Experimentally, the CD spectra of 31b and 31c with additional methyl groups in positions 1 and 18 have been observed. However, these groups influence the CD not significantly so that we discuss here the compounds 31e-g investigated theoretically.
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