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Fragmentation of 6‐Deoxy‐6‐halo‐hexono‐1,5‐ortholactones: A Concerted, Nonstereospecific Process
Author(s) -
Bernet Bruno,
Vasella Andrea
Publication year - 1984
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19840670519
Subject(s) - chemistry , lone pair , fragmentation (computing) , halo , oxygen atom , stereochemistry , ring (chemistry) , crystallography , molecule , organic chemistry , physics , quantum mechanics , galaxy , computer science , operating system
The synthesis of the D ‐ arabino ‐ and D ‐ ribo ‐ortholactones 13a–f and 15b–f and their treatment with Zn leading to the unsaturated esters 14a–d and 16a–d are described. Possible fragmentation mechanisms are discussed. The results were only compatible wit a concerted, nonsynchronous process, where both the axial lone pair of the ring oxygen atom and the lone pair formed during rupture of the C(5), O‐bond participate in the elimination of the axial and of the equatorial C(1)‐alkoxy groups, respectively.