Tetrahedron p. 8107 - 8118 (1993)
Update date:2022-09-26
Topics:
Stern, Alfred G.
Ilao, Martin C.
Nickon, Alex
Homobrexan-2-one was synthesized labeled in the α-position with 13C and also with an axial or equatorial D.Their p-tosylhydrazone Li salts were thermolyzed and photolyzed (Bamford-Stevens reaction) to generate putative singlet carbenes, which undergo competitive 1,3-insertion to a tetracycle and 1,2-H (or D) shift to an alkene.After correction for isotope effects, the Hax/Heq shift ratios were ca. 1.7 and ca. 1.2 for the thermal and photic processes, respectively.These ratios are free of chair-boat and epimerization ambiguities.
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