By C. Rüchardt, Steric Effects, L. Birkofer, O. Stuhl, K. A. Muszkat, N. T. Anh
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Extra resources for 88 Topics in Current Chemistry: Organic Chemistry Syntheses and Reactivity
O. calculation 49). 110 The 4 a,4 b-Dihydrophenanthrenes 3 Vibrational Structure As was mentioned previously, the first absorption band (I) of 4 a,4b-dihydrophenanthrene is usually structureless and rather broad, having a half height width (&Xl/2) of 4700 cm - l in 1. This band shows vibrational structure (developed to various extents) only in 12, 13, 15, 37, 38, 40, 43-46, and in 49-53 (see Table 13). The observed vibrational spacings, usually 1 2 0 0 - 1 4 0 0 cm -1, correspond very probably to an excited state-totally symmetric stretching mode (vs) of the C - C double bonds such as t~ Vs whose frequency would be lower than the frequency o f the same mode in the electronic ground state.
22) * 97 K. A. Muszkat Table 4. 4a,4b-Dihydrophenanthrenes. 7 (~ 8000). In MCH/IH (10 - 5 M) h i 334 at - 1 0 o , e 50%. 5 Ref. 7. 03 h, Ref. 5;r25 55 h, Ref. 6 at - 1 8 5 ~ 10 - 5 M in MCH/IH, h i 334 - c 25%. 5,E o 3. 2. 8 min, rtex. 7 mitt, Ref. 7; r2S 102 min, Ref. 23) 98 The 4 a,4 b-Dihydrophenanthrenes Table 5. 4a,4b-Dihydrophenanthrenes. Systems with five conjugated rings derived from 1,2-dinaphthylethylenes 9 10 6 5 ~. 003 (hi 313), Ref. 5, Ref. 06 (h i 334), 0o 1. 5, Ref. 06 ( - 5 0 ~ 10 - 3 ( - 160~ Ref.
Soc. : Pure Appl. Chem. 41, 145 (1975) 76. Barton, D. H. R. : J. Am. Chem. Soc. 98, 3036 (1976) 77. : Adv. Photochemistry 2, 263 (1964); Mihailovic, M. : Heteroeycles 3, 1035 (1975); Hesse, R. , Adv. Free Rad. Chem. 3, 83 (1969) 78. Wilt, J. : in Kochi, J. , Free Radicals, Vol. 1, p. 333, New York: Wiley 1973 79. : Chem. Ber. 108, 1421 (1975) 80. : Angew. Chem. 88, 159, 161,723 (1976); Angew. Chem. Int. Ed. Engl. 15, 173, 174, 688 (1976) 81. Private communication of Prof. Giese, Darmstadt 82. : J.
88 Topics in Current Chemistry: Organic Chemistry Syntheses and Reactivity by C. Rüchardt, Steric Effects, L. Birkofer, O. Stuhl, K. A. Muszkat, N. T. Anh