The preparation of C-1 and C-2 methylated acenaphthenes

Abstract

The syntheses of I-methyl-, 1,l-dimethyl-, cis(?)-l,2-dimethyl-, 1,1,2-trimethyl-, and 1,1,2,2-tetramethylacenaphthene have been accomplished by standard reactions from the two compounds l-acenaphthenone and Zmethyl-1-acenaphthenone. These two ketones were in turn obtained from l-naphthaleneacetic acid.

The effects of ionic liquids on the ethanolysis of a chloroacenaphthene. Evaluation of the effectiveness of nucleofugality data to predict reaction outcome

“…The chloride 1 was prepared from acenaphthene through oxidation, methylation, reduction and chlorination, as per literature procedures. [52][53][54][55][56] Ethanol and triethylamine were puried through distillation according to literature procedures, 57 and stored over activated 3 Å molecular sieves until use. The ionic liquids 3-5, 8 and 9 were prepared as per literature procedures, 39 through alkylation of the appropriate amine followed by anion metathesis.…”

Stereochemical Control of Reductions. 9. Haptophilicity Studies with 1,1-Disubstituted 2-Methyleneacenaphthenes

“…Extraction with Et 2 O both before and after acidification yielded 38.38 g (96%) of 4 (R = Me) as a white solid: mp 141−143 °C (lit. 152−3 °C, 140−142 °C); IR (CHCl 3 ) 3500−2200 (br), 1747, 1710 cm -1 ; 1 H NMR (400 MHz) δ 8.08 (1 H, d, J = 7.7), 7.87 (1 H, d, J = 8.5), 7.78 (1 H, d, J = 7.7), 7.50 (4 H, complex), 4.54 (1 H, q, J = 6.8), 1.67 (3 H, d, J = 6.8); MS (EI), m / e (relative intensity) 599.2 (13), 400.2 (24), 399.2 (100), 200.2 (6), 199.2 (43), 155.1(22); HRMS (EI) calcd for C 13 H 12 O 2 200.0837, found 200.0841.…”

Acenaphthene chemistry. 2. Synthesis and antiinflammatory activity of 1-[2-(dimethylamino)ethyl]-2,2-dimethyl-1-acenaphthenecarboxamide

“…Oxidation of 2,2-DimethyI-l-hydroxymethylacenaphthene (3).s -A soln of 3 (70.9 g) in Me«CO (3.55 1.) was cooled to -5°in an MezCO-Dry Ice bath, and treated rapidly with 355 ml of Jones reagent through a dropping funnel.…”