A DIRECT SYNTHESIS OF Γ,γ-Dimethylpimelic ACID

Conformational analysis. 34. Carbon-13 nuclear magnetic resonance spectra of saturated heterocycles. 6. Methylthianes

“…2-Methylthiane (2). N-Benzoyl-2-methylpiperidine was synthesized in 90% yield from 2-methylpiperidine, benzoyl chloride, and sodium hydroxide following á procedure described for A'-benzoylpiperidine,32 bp 165-168 °C (1.2 Torr), mp [43][44][45] °C (lit.33 44-45 °C). This material was converted to 1,5-dibromohexane by phosphorus tribromide-bromine in 70% yield,34 bp 110-113 °C (18 Torr) (lit.35 153-154 °C (100 Torr)).…”

Conformational analysis. 35. S-Alkylthianium salts

“…rac-1 -Benzyl-trans-2,Zrans-6-DimethyIthianium Tetrafluoroborate (44). Following the above procedure, 0.01 mol of m-2,6-dimethylthiane was allowed to react with 0.01 mol of benzyl bromide and 0.01 mol of silver tetrafluoroborate/acetonitrile complex for 7 days in the dark.…”

Substituent effects and the di-.pi.-methane rearrangement. Mechanistic and exploratory organic photochemistry

“…This and the ubi-quity3 of the di-x-methane rearrangement provided suggestive evidence for 1,1-di-p-cyanophenyl-2,2-dimethyl-3-(2,2-di-p-cyanophenylvinyl)cyclopropane as the structure of photoproduct 16. Unambiguous evidence was provided by the degradation and synthesis outlined in Chart III. Thus, treatment of photoproduct 16 with the Sam-Simmons permanganate-crown ether reagent6 led to an acid, mp 234-236°. The nmr revealed two nonequivalent methyl absorptions at r 8.51 and 8.88 and a methine singlet at r 7.64.…”

“…Fractions 8-13 gave 0.737 g of crude diene which was recrystallized from ether-ethanol to give 0.572 g (62.9%) of the desired diene, mp 162-164°. The spectral data were the following: ir (CC14) 6.40, 6.72, 7.13, 9.17, 9.88, and 12.17 µ; nmr (CDCI3) 2.55-3.15 (m, 16 H, arom), 4.10 (s, 2 H, =CH), and 8.98 (s, 6 H, CH3), 1,1,5,5-T etra-p -cyanopheny 1-3,3-dimethyl-1,4-pentadiene. A solution of 5.28 g (9.82 mmol) of 1,1,5,5-tetra-p -chlorophenyl-3,3dimethyl-1,4-pentadiene and 15.2 g (0.180 mol) of cuprous cyanide in 60.0 ml of N-methyl-2-pyrrolidone18 was refluxed 70 hr with Trubore stirring under nitrogen.…”

“…The spectral data were the following: ir (CHCI3) 4.47, 6.35, 6.68, 8.81, 9.02, 11.03, and 11.97 µ; nmr (CDC13) 2.25-3.15 (m, 16 H, arom), 3.98 (s, 2 H, =CH), and 8.92 (s, 6 H, CH3); uv XmaxH268 (e 39,300).…”