By C. Rüchardt, Steric Effects, L. Birkofer, O. Stuhl, K. A. Muszkat, N. T. Anh
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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. 7, Ref. 14 (h i 313), Ref. 24b) 99 K. A. Muszkat Table 6 . 24e) '2 + 3' B, from 1-(2-naphthyl)-2-(3-phenanthryl)ethylene, MCH, k i 313;c 30% h m a x , I : 545, (e 12,000) 510, 475; II: 389, 360, 335.
Butyl radicals is diffusion controlled and requires no activation. Observed large solvent and temperature dependences of kd/k e were ascribed to anisetropic reorientation motions of the radicals during their encounter in the solvent cage. This may also be the reason for the low probability of recombination of 2-cyano-2-propyl radicals as deduced from CIDNP-experiments t tg). Recently, an interesting example of stereoselective radical dimerization was described which awaits explanation. It was found that radical 49 (X = p-C1; R = t-butyl) dimerizes diastereoselectively120) to the more stable D, L-diastereomer in contrast to other radicals 49 with smaller side chains R.
Under such conditions the NMR signals due to the nuclei of the DHP derivative are identified as those which disappear following photochemical ring cleavage (process B). This process yields only the cis-isomer of the parent ethylenic compound. In addition to their structural value, NMR studies in this field allow to verify the conversion estimates obtained from optical studies 11, 14). In 61, 62 and 64 proton NMR proves that photocyclization takes place between 1 and 1' atoms and not for instance between atoms 1 and 8' or between atoms 8 and 8' (numbering as in 61 in Table 8).