crystallzed from EtOAc, m.p. >300"C, m/z (EIMS) 502; 'H-NMR (CDCI,): 6 = 1.81 (m. 4H). 2.33 (m, 4H), 2.61 (m, 4H), 4.92 (s, 4H), 4.97 (bs, 4H), 4.99 ( s , 4H). 5.09 ( s , 4H), 6.99 (s, 2H); "C-NMR (CDCI?): 6=25.7, 43.2, 85.0, 85.3, 100.9, 110.2, 143.1, 144.2, 144.61. 6a: 6 (156 mg, 0.88 mmol) was heated under reflux (48 h, N2) with anthracene (50 mg, 0.28 mmol) in xylene (5 mL): yield of the crude product: after chromatography (SiO,/CHCI,-Et,O) 17 mg, I Io/i. Colorless crystals [m.p. >300"C), m/z (positive ion FABMS) 535 for (M+H)O] suitable for X-ray crystallography, were grown by the vapor diffusion method (CHCI,. CICHzCH,Cl-light petroleum). Reaction (CH2Cl2,10 kbar, 55-60"C. 200 h) of 7 (373 mg, 0.74 mmol) with 5 (156 mg, 0.74 mmol) yielded, after chromatography (SiO2/CHCl3-MeOH), 8 [I05 mg, 20%, recrystallized from CHCI?, m.p. > 300"C, m/z (positive ion FABMS) 713 for (M+H)@: 'H-NMR (CDCI,): 6=1.62 (m, 4H), 2.32(m,8H),2.63(m,8H),4.89(~,8H),5.08(~,4H),6.98(~,4H): "C-NMR (CDC13): 6=27.1, 44.2, 84.8, 86.6, I10.1, 144.6, 152.51, which was also obtained in very low yield (3.5%) by heating 6 under reflux (48 h, N2) in xylene. Single crystals, suitable for X-ray analysis, were obtained by slow evaporation of a chloroform solution of 8 at room temperature. German version: Angew. Chem. 99 (1987) 941 Champions of highly speculative projects are few and far between; here, they were Dr. R . D. Handscombe (University of Sheffield) and Prof. G. Stagno dXlcontres (University of Messina). We thank them for their moral support-and for their enthusiastic efforts, a// the many postgraduate students, who over the years, have received their introduction to the research laboratory in Sheffield making starting materials for "the crazy molecule". One of the authors (J. F. S.) also thanks the Leverhulme Trust for the award of a Research Fellowship.
:Recently, some force-field calculations have been carried out (R. W.Alder, R. B. Sessions, J. Chem. Sac. Perkin Trans. 2 1985, 1849) on molecular belts built from cyclohexa-1,4-diene rings. Compounds of the type 1 were referred to in the above paper as [nlbeltenes; the strain energy per 2-butene-l,2,3,4-tetrayI unit was found to decrease monotonically from [3]beltene to [12]beltene. Calculations on encapsulated complexes of small molecules led to the prediction that, in the case of acetylene, for example, [9]beltene will be the optimum molecular receptor.