ULTRAVIOLET ABSORPTION SPECTRA OF SOME VINYLNAPHTHALENES AND RELATED AROMATIC HYDROCARBONS^{1, 2, 3}

A computational study of the reactivity of diethenylnaphthalenes towards anionic polymerization

“…18 Klemm et al concluded on the basis of ultraviolet spectroscopy that 1-vinylnaphthalene exists in a non-planar anti conformation, 1-anti whereas 2vinylnaphthalene exists in a coplanar conformation 2-syn. 12 Similar conclusions were reached on the basis of 1 H NMR chemical shifts. 19 On the basis of proton-proton nuclear Overhauser effects, it was concluded that the minimum energy conformation for 1-vinylnaphthalene was 1-anti with the deviation of the torsion angle α from planarity being equal to 38Њ.…”

“…The high resolution NMR spectra of 1-vinylnaphthalene have been used to deduce a value of 36.7-45.9Њ for the angle between the vinyl group and the ring planes. 12 The value calculated by AM1 is 40.1Њ whereas PM3 has set this value to 0Њ. Based on these findings, AM1 has been chosen for further investigations.…”

Ab + D → Abd → Abcd

“…Normal adducts would have a A 8(14) -double bond, but under the conditions of the reaction this isomerizes to Δ 8 , reestablishing the naphthalene ring system. The location of the R group (at C-15) is the result of the greater stability of 263 compared to the tautomer that would condense to a 13-R adduct [192,193]. This "undersired" type of product was obtained also from 259, which gave rise to 265 [176,194,195].…”

Clemmensen reduction of 2-acetonaphthone

“…Caled for C24H20O: C, 88.85; N, 6.21. Found: C, 88.66; H, 6.37. 2,2-Di(2-naphthyl)butane (8).•-Mp 90-92°; ir (Nujol) 6.15, 6.27, 7.72, 7.87, 8.38, 8.87, 10.56, 11.69 and 12.22 µ; mass spectrum (70 eV) m/e (rel intensity) 310 (21), 282 (24), 281 (100), 266 (16), 265 (22), and 153 (15); nmr (CC14) 7.82-6.82 (m, Í4, ArH), 2.28 (quartet, 2, -CCH2CH3), 1.69 (s, 3, -CCH3), 0.73 (t, 3, -CH2CH3); uv max (95% EtOH) 217 nm (log e 4.99), 231 (5.05), 235 (5.08), 266.5 (4.11), and 275.5 (4.10).…”