Acknowledgment. We express our appreciation to Dr. U. Weiss for valuable discussions.Registry No. (S)-(-)-2a, 65915-63-1; (S)-(-)-2b, 84580-10-9;(S)-(-)-3, 84499-95-6; (±)-4a, 79605-67-7; (S)-(-)-4a, 84580-11-0; (S)-(-)-4a camphanate, 84520-47-8; (S)-(-)-4b, 78341-38-5; 5, 6786-30-7; (S)-(-)-6a, 84499-96-7; (S)-(-)-6b, 84499-97-8; (S)-(-)-7, 55095-00-6; 8, 829-14-1; (S)-(-)-9a, 84499-98-9; (S)-(-)-9b, 84499-99-0; (fi)-(+)-10,84500-00-5; (S)-(-)-10,84500-01-6; (±)-lla, 62249-35-8; (fi)-(-)-lla, 62210-83-7; (fi)-H-lla camphanate, 84580-12-1; (R)-(-)-llb, 84580-13-2; benzocyclohepten-3-one, 826-73-3.

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is representative. Into a three-necked 500-mL, round-bottomed flask, equipped with a cold-finger condenser charged with solid C02 and ethanol, a nitrogen inlet, and a magnetic stirrer, was condensed ~250 mL of ammonia. To the ammonia was added t-BuOH (9.74 mmol) and Na metal (9.74 mol) to form sodium tert-butoxide and then PhCH2SH (9.74 mmol). To this solution was added 2-chloroquinoline (4.86 mmol), and the solution was irradiated for 90 min. The reaction was quenched by adding Mel (9.7 mmol), and the ammonia was allowed to evaporate. Water (100 mL) was added to the residue, and the mixture was extracted three times with 50 mL of diethyl ether. The ether extracts were dried and distilled. The residue was column-chromatographied on silica gel and eluted with petroleum ether. 2-Quinolyl benzyl sulfide was obtained as a white solid and was recrystallized from petroleum ether: mp 39-41 °C (lit.26 mp 44-45 °C); hydrochloride,

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14) Yet another possibility would be to use a reducing agent that would cleave the N-0 bond of the isoxazoline first and then effect reduction of the C-N bond. Sodium in ethanol is known to operate in this fashion. At present, however, we have not been able to obtain desirable products from this reduction procedure. See, for example, Jáger, V.; Buss, V. Justus Liebigs Ann. Chem. 1980,101. (15) Reduction of isoxazolines by lithium aluminum hydride is believed to involve Li-O complexation during hydride transfer, see: Jáger,