Journal
MONATSHEFTE FUR CHEMIE
Volume 141, Issue 12, Pages 1347-1351Publisher
SPRINGER WIEN
DOI: 10.1007/s00706-010-0410-5
Keywords
Oxidation; Molecular modeling; Cyclization; Mass spectrometry; Tartaric acid; Organocatalysis
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Funding
- FWF (Austrian Science Funds) [P22508-N17]
- Austrian Science Fund (FWF) [P 22508] Funding Source: researchfish
- Austrian Science Fund (FWF) [P22508] Funding Source: Austrian Science Fund (FWF)
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Attempted oxidation of a TADDOL-derived bisthioacetate resulted in a rather unexpected and remarkable cyclization and deprotection reaction, giving a thiolane-1,1-dioxide as the main product. Systematic in situ ESI-HRMS studies revealed a bicyclic, highly acid labile key intermediate of this reaction. Supported by force field calculations, the high sensitivity of this intermediate was judged to be due to the formation of a highly strained trans-configured bicyclo[3.3.0]skeleton.
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