By C. Rüchardt, Steric Effects, L. Birkofer, O. Stuhl, K. A. Muszkat, N. T. Anh
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15, 167 (1967); Nonhebel, D. , Walton, J. : Free Radical Chemistry, p. 533ff. Cambridge: University Press 1974 92. Clark, D. , Scanlan, J. , Walton, J. : Chem. Phy~ Lett. 53, 102 (1978) 93. Tedder, J. , Walton, J. : Aec. Chem. Research 9, 183 (1976) 94. Brown, H. : Organic Synthesis via Boranes, New York: Wiley 1975; Davies, D. , Parrott, J. , Free Radicals in Organic Synthesis, Berlin-Heidelberg-New York: Springer 1978 95. : Chem. Ber. 110, 2588 (1977) 96. Jenkins, A. : Adv. in Free Radical Chem.
10. Ref. 09, Ref. 35. Ref. 11, 13)* l! 15)Sh, r _ 31 o 2 h, r_10 10 rain, Ref. 13)* t2 Me M~ eMe Me 15 94 from 2,2',4,4',6,6'-hexamethylstilbene, 4 x 10-4M, MCH/IH, h i 280 c 21% at +10 ~ Xma x (e)I: 475 (3100) II: 320 (7100), 310 (7000) III: 245 (15 800). tr. 4 (280). 1 I, 14) Me from 3,5,3',5'-tetramethylstilbene in MCH/IH UV a at - 1 8 0 ~ c 20%. 245 r_120 6 m i n ; r _ 1 6 0 = 43 rain Ref. 55) measured at - 1 8 0 ~. Ring opening with ;~ 436 at - 1 8 0 ~ * Ref. 15) T h e 4 a,4 b - D i h y d r o p h e n a n t h r e n e s Table 1 (continued) (~~OMe I6 see 4 m e t h o x y - D H P .
The activation energies for the process Y ~ DHP are of the order of 15 kcal/mole. The visible absorption band in these conformers is slightly red shifted relative to the stable forms, but the intensities of the vibrational components are quite similar. Very recently 24b), an energy minimalization exploration of the potential surface of 44 has revealed the presence of a higher energy conformer derived from the previously suggested geometry49). These two conformers of 44 differ significantly in their H14 - HI s and H4a - H14 distance 24b).
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