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5.33 (d, J = 10.2 Hz, 1 H, 1-H), 3.11 (d, J = 2.4 Hz, 1 H, 8-H),
2.08 (s, 3 H, CH3) ppm. 13C NMR (100.6 MHz): δ = 143.3 (C-2),
139.1 (C-5), 134.8 (C-3), 123.3 (C-4), 121.3 (C-1), 110.0 (C-6), 94.9
(C-9), 83.0 (C-7), 80.7 (C-8), 73.5 (C-10), 4.4 (C-11) ppm. IR (film):
[14]
ν = 3310 (vs), 2920 (m), 2230 (w), 1550 (s), 1255 (m), 1210 (m),
˜
990 (s), 950 (s), 910 (s) cm–1. UV (acetonitrile): λmax (lgε) = 311
(3.90), 297 (3.96), 286 (3.87), 257 (3.61), 243 (3.66), 231 (3.68), 215
(3.75), 201 (3.85) nm. MS (EI, 70 eV): m/z (%) = 142 (42) [M]+,
141 (100), 139 (111), 127 (10), 115 (74), 63 (12). C11H10 (142.19):
calcd. C 92.91, H 7.09; found C 92.35, H 7.29.
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[7] Although this reaction type was known much earlier [R. Paul,
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[10] For a summary of the tetramethyleneethane (TME) diradical
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