of 0.08 M potassium hydride/THF, 0.30 mmol of 12, and 0.30 mmol of 18-crown-6 ether was degassed and sealed in a glass tube. The tube was heated at 80 °C for 48 h. The reaction mixture was diluted with water and extracted with ether. The ether extract was washed with water, dried, and concentrated, leaving 85 mg (98% recovery including 10% unreacted 12) of a white solid, mp 80-95 °C. Spectral Characterizations of Elimination Products. The 'H NMR spectra of elimination product mixtures (23 + 24) show pairs of partially resolved doublets for the bridgehead protons (H, in 23 and 24) in the region & 4.9-5.2. The vinyl protons lie within the aromatic regions (approximate b 7-8). The methylene protons absorb as varying types of multiplets for products from 12 (5 2.8-3.9), four sets of triplets for products from 20 (5 2.9,3.1, 4.2,4.4), and two singlets for products from 22 (b 4.8). In the case of vinyl chlorides from 22 the area integrations for the two singlets could be used to confirm the product isomeric distribution from analyses of the bridgehead proton absorptions.

A new approach to the synthesis of monocyclic /3-lactam derivatives is presented. Dipolar cycloaddition of an aldonitrone with TMS-acetylene provided a 5-(trimethylsilyl)isoxazoline. The isoxazoline was fragmented with tetrabutylammonium fluoride (TBAF) to provide monocyclic /3-lactam derivatives in modest yield. Fragmentation of the isoxazoline with aqueous HF provides excellent yields of ,/3-unsaturated amides.

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Nineteen derivatives of (1 R)-(+)camphor with deutero, fluoro, bromo, iodo, keto, and hydroxyl functionalities at carbons 3, 5, 8, or 9 have been examined using 13C NMR. The chemical shifts for each carbon of these substituted camphor derivatives have been assigned using broad band decoupling and the refocused INEPT pulse sequence. INTRODUCTIONThe importance of norborneol derivatives to the understanding of the 13C NMR of other bicyclic systems has been well established.'In the course of our recent studies of the metabolism of camphor by the cytochrome P-450-CAM273, nineteen derivatives of (1R)

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