Hybridization in propellanes

Non‐empirical calculations of NMR indirect carbon–carbon coupling constants: 2. Strained polycarbocycles

“…Published estimations of its orbital hybridization 50,51 fall into a wide and ambiguous range between sp 0.5 -sp 0.5 and sp 5 -sp 5 . A further and more straightforward guide could be gained from the present high-quality calculations of J(C,C) between bridgehead carbons in propellane treated on the grounds of the multipath coupling mechanism.…”

The bond between inverted carbon atoms. Synthesis and chemistry of 2,4-methano-2,4-didehydroadamantane: a highly reactive [3.1.1]propellane

“…169.1 (s), 154.2 (s), 104.5 (t), 76.6 (d), 43.1 (d), 39.3 (t), 38.1 (d), 36.7 (t), 33.8 (t), 32.0 (d), 31.6 (t), 27.7 (d), 20.9 (q) 155.7 (s), 103.4 (t), 83.6 (d), 55.3 (q), 42.9 (d), 39.5 (t), 38.6 (d), 36.9 (t), 33.5 (t), 31.8 (d), 31.4 (t), 28.0 (d) 4.96 (br s, 1 11), 4.63 49.7 (d), 40.7 (d), 40.0 (t), 35.0 (t+d), -2.5-1.1 (nr) 34.6 (t), 31.7 (t), 30.2 (t), 27.6 (d), 25.3 (d) 8c 79.2 (s), 50.1 (q), 42.7 (d), 35.4 (d), 35.1 (t), 3.07 (s, 3 ), 2.3-1.0 (in, 15 H) 34.8 (t), 32.7 (t), 31.7 (t), 31.1 ((), 30.1 (d), 29.0 (d), 26.3 178 (M+, 100), 135 ( 27), 109 (59), 105 (30). 91 (70), 79 (78), 77 (65)…”

“…144.5 (s), 134.7 (s), 129.8 (d), 129.5 (d), 63.3 (s) , 61.9 (s), 50.1 (d), 42.1 (t), 39.6 (d), 35.0 (t) , 32.4 (t), 30.9 (t), 28.4 (d), 27.7 (t), 24.5 (d), 21.3 (q) 135.9 (d), 133.9 (s), 128.7 (d), 127.8 (d), 54.6 (s) , 43.8 (d), 36.9 (t), 36.2 (d), 36.0 (d), 34.9 (t) , 34.6 (t), 32.5 (t), 30.7 (t), 28.8 (d), 25.9 (d)…”

Synthesis of propellane-containing natural products

“…In addition to Wiberg's results, other theories have also been suggested. 18,[24][25][26][27] Ginsburg [28][29][30] and Wiberg 19,31,32 have reviewed the syntheses and the theoretical studies of propellanes extensively, Wiberg concentrating on the small-ring propellanes and Ginsburg on the medium-sized rings. In his book entitled 'Propellanes', Ginsburg even describes the syntheses and structures of natural products possessing the propellane structure.…”