Synthesis of 1,2-cyclononadien

Preparation of 1,2-cyclononadien

Preparation of 1,2-cyclononadien

Preparation of 1,2-cyclononadien

To a stirred reaction mixture consisting of 55.0 gm (0.50 mole) of cis-cyclooctene and 41.5 g (0.125 mole) of carbon tetrabromide cooled to —65° C is added 74.0 ml (0.125 mole) of methyllithium in ether over a 45 min period. After stirring at -65° C to — 68° C for an additional 0.5 hr, another 80.5 ml (0.135 mole) of methyllithium is added over a 0.5-hour period. The re­action mixture is stirred for another 0.5 hr at — 68 °C, warmed to 0° C, water added, the ether separated, washed with water until neutral, dried over sodium sulfate, and then fractionally distilled to afford 11.3 g (74 %), b.p. 62°-63°C (16 mm), nD 1.5060 at 20 ° C.

L. Skattebol, J. Org. Chem. 31, 1554 (1966).

Preparation of 1,2-cyclononadien

Preparation of 1,2-cyclononadien

To a glass vial is added a solution of 3.75 gm (0.015 mole) of 1-bromo-2-chlorocyclodecene in 35 ml of absolute ether. Then 1.0 g of fine sodium wire, cut into 1 cm lengths, is added. The tube is sealed after flush­ing with nitrogen, and after 10 days at room temperature, with occasional shak­ing, the tube is broken open, filtered, washed once with a saturated salt solution, twice with hydrochloric acid, once again with salt solution, dried, and then fractionally distilled to afford 1.0 g (49%), b.p. 72°-75°C (13 mm), nD 1.5024 at 20 ° C, d=0.897at 20 ° C.

T. Blomquist, R. E. Bruge, Jr., and A. C. Sucsy, J. Amer. Chem. Soc. 74, 3636 (1952).

IUPAC Name

cyclonona-1,2-diene

InChI

InChI=1S/C9H14/c1-2-4-6-8-9-7-5-3-1/h1,5H,2,4,6-9H2

InChI Key

YHGPUHUSTRYSIC-UHFFFAOYSA-N

Canonical SMILES

C1CCCC=C=CCC1

Depositor-Supplied Synonyms

1,2-Cyclononadiene, cyclonona-1,2-diene, 1123-11-1, 26114-92-1, AC1L39IZ, [R, ]-1,2-Cyclononadiene, CTK0I1753, [R,(+)]-1,2-Cyclononadiene, [S,(?)]-1,2-Cyclononadiene, YHGPUHUSTRYSIC-UHFFFAOYSA-N, ZINC66377680, OR109690, InChI=1/C9H14/c1-2-4-6-8-9-7-5-3-1/h1,5H,2,4,6-9H, 18526-52-8

Removed Synonyms

CID136899

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