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Volumn 63, Issue 25, 1998, Pages 9190-9196

A sulfoxide-based ring annelation approach to fused, many-membered ring N,S-heterocycles

Author keywords

[No Author keywords available]

Indexed keywords

2 MERCAPTOBENZOTHIAZOLE; ACID ANHYDRIDE; METHANOL; PYRROLE DERIVATIVE; SULFENIC ACID DERIVATIVE; SULFONIUM DERIVATIVE; SULFOXIDE;

EID: 0032509455     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9805044     Document Type: Article
Times cited : (26)

References (59)
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    • However, the intervention of sulfenic acid chemistry must again be considered, especially in light of the report (Lee, W. S.; Hahn, H. G.; Nam, K. D. J. Org. Chem. 1986, 51, 2789) that only the "cis" diastereomer, which readily forms a sulfenic acid intermediate, undergoes a ring-opening reaction, whereas the "trans" isomer reacts only under much harsher conditions. This behavior parallels the observation that "cis"-18a forms a macrocycle, but the "trans" isomer (18a′) does not. Nonetheless, sulfenic acid intermediates must be considered improbable because direct cyclization of an open-chain sulfenic acid such as i to a nine-membered ring in high yield seems unlikely. Additional experiments are underway to study the chemistry of sulfenic acid derivatives such as i generated from trapped sulfenic acids. (Chemical Equation Presented)
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