Abstract
Abstract The origin of the hydrogen atoms implicated in the single and double hydrogen rearrangements (leading to [C6H9O]+ and [C6H8O]+ ions, whose relative abondance is typical of the phosphorus configuration) was investigated by means of selective deuteriation of the β and γ carbon (relative to phosphorus) of the isomeric 2,4,7-trioxa-3-methyl-3-phospha-3-thionobicyclo (4,4,0) decanes 1a and 1b. For both isomers the β hydrogen atoms are involved predominantly in the single hydrogen rearrangement. In the case of the double hydrogen rearrangement the hydrogens H1 (β) and H10, H10'(γ) for the a isomer and H6(γ) and H10, H10'(γ) for the b isomer are preferentialy transferred. The proposed fragmentation mechanisms attempt to explain the effect of the P[dbnd]S bond orientation on the fragmentation stereospecificity. La recherche de l'origine des atomes d'hydrogene impliques dans les fragmentations avec rearrangement a un ou deux atomes d'hydrogene (conduisant aux ions [C6H9O]+ et [C6H8O]+ dont l'abondance rel...
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