Hydroxide-ion-initiated reactions under phase-transfer catalysis conditions. 9. Dehydrohalogenation of (haloethyl)benzenes by quaternary ammonium salts

✍ Scribed by Halpern, Marc; Zahalka, Hayder A.; Sasson, Yoel; Rabinovitz, Mordecai

• Book ID: 126877054
• Publisher: American Chemical Society
• Year: 1985
• Tongue: English
• Weight: 648 KB
• Volume: 50
• Category: Article
• ISSN: 0022-3263
• DOI: 10.1021/jo00225a019

✦ Synopsis

In addition, 14 (7 mg, 8%) was obtained. 4-tert-Butyl-l-hydroperoxy-9-oxabicyclo[4.2.l]nonanes (16 and 17). A solution of 14 (92 mg, 0.50 mmol) was rearrnged in THF (2 mL) and 90% H20z (2 mL, 72 mmol HzOz) containing TsOH.H,O (120 mg, 0.60 mmol) for 48 h according to procedure F. Preparative TLC of the crude product (50 mg) yielded an inseparable mixture of 16 and 17 (31 mg, 33%) as a 1:l mixture by 'H NMR as shown by integration of the carbinyl signals at 6 4.17 ( 16) and 4.70 (17).

4-tert-Butyl-l-hydroperoxy-9oxabicyclo[4.2.l]nonane (17). A solution of 15 (44 mg, 0.24 mmol) was rearranged in THF (1 mL) and 90% HzOz (1 mL, 36 mmol HzOz) containing TsOH-H20 (24 mg, 0.12 mmol) for 20 min according to procedure F. Preparative TLc of the crude product (64 mg) yielded 17 (43 mg, 84%