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modifications of known procedures.5-' Reduction of 10 with lithium aluminum hydride gave an alcohol (11, 96 z yield)* which was converted to p-nitrobenzenesulfonate ester 5 uia the sodium alkoxide of 11 (from sodium hydride-tetrahydrofuran) and p-nitrobenzenesulfonyl chloride (2 equiv) in tetrahydrof~ran.~ The yellow crystalline sulfonate ester (5) is obtained in 92 yield, mp 143-144". ences in the fine structure of the nmr and ir spectra. Both bridgehead olefins are probably produced by the Hofmann route, and, by analogy with the t h e r m o l y~i s~~ of 1 -bicyclo[4.2.l]nonyltrimethylammonium hydroxide, it is likely that the A'(') olefin is the major olefin from this reaction. Thus, we conclude that bridgehead olefin 1 is formed in good yield from the thionocarbonate 13 and that both bridgehead olefins 1 and 2 are probably formed in small amounts in thermolysis of quaternary ammonium hydroxide 4. We are continuing to investigate synthetic routes to 1 and 2 in the hope that we can prepare them under mild conditions and record their spectra.

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