Possible effect of hyperconjugation on solvolysis rates of benzhydryl chlorides and spectra of related compounds

Gattermann reaction of 3,5-dimethoxyphenylacetonitrile. Synthesis of 6,8-dioxyisoquinolines

“…The rate of hydrogen uptake varied considerably over several (11) K. Nakanishi, M. Ohashi, S. Kumasaki, and H. Koike, Bull. Chem.…”

“…(in cm"1) 3100 (C-H), 2230 (C=CCN), 1630 (C=C), 1570 (pyridine); X*T" (*) 241 µ (11,500), 275 (6100); nmr (CCli in ppm) three-proton doublet (J = 7 cps) at 2.18 (CHCH3), one-proton quartet (J = 7 cps) at 7.19 (=CHCH3), three-proton multiplet at 7.35-7.80 (PyH3, H4, Hs), one-proton doublet at 8.45 (PyH6).…”

“…-A 1,6-g sample of 2-(4'-pyridyl)-3-hydroxy-2-butenonitrile (11) was treated as described above (methyl iodide in place of ethyl iodide) to produce 1 -methyl-4-( acetylcyanomethylidene) -1,4dihydropyridine (12) as pale yellow crystals after recrystallization from ethyl acetate: mp 216-217°; PKBr (in cm-1) 3100 (C-H), 2200 (C=C-CN), 1660 (C=C-C=0), 1600 (C=C); X°""6-9 (e) 235 µ (15,400), 362 (35,000); '",1 (ej 230 µ (12,800), 362 (22,400); nmr (DMSO-de) (in ppm) three-proton singlet at 2.35 (CH3C=0), three-proton singlet at 4.03 (GHYN), fourproton doublet at 7.95 (ring ).…”

Photophysics of phenylcyclopropanes, styrenes, and benzocycloalkadienes

“…A previous study of the benzocycloalkenes series benzocyclobutene through benzocyclooctene revealed the lack of parallel change between the 'Lb 0-0 band X and <. 21 Groundstate strain effects26 may be responsible for the absence of a common direction and magnitude of change between Xmax and emax in both the benzocycloalkene21 and benzocycloalkadiene series.…”