Synthesis of new cyclic dialkoxy disulfides

Journal of Organic Chemistry

Volumn 71, Issue 17, 2006, Pages 6659-6661

  Eghbali, Nicolas ^a   Bohle, D Scott ^a   Harpp, David N ^a  

^a MCGILL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

COMPOSITION; MOLECULAR STRUCTURE; SULFIDE MINERALS; SYNTHESIS (CHEMICAL); X RAY ANALYSIS;

CYCLIC DIALKOXY DISULFIDES; FURANDIMETHYLENE DIALKOXY DISULFIDE.; X RAY STRUCTURE;

ORGANIC COMPOUNDS;

2,3 FURANDIMETHYLENE DISULFIDE; CYCLIC DISULFIDE DERIVATIVE; DISULFIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CYCLIZATION; ISOMER; STRUCTURE ANALYSIS; SYNTHESIS; X RAY ANALYSIS;

EID: 33747410126     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060944s     Document Type: Article

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25. 2 was optional as it proceeds well at room temperature.
26. An attempt to isolate and characterize these molecules by FTMS was made but results were not conclusive. For instance, the oligomer from 13a could not be detected but instead elimination and substitution products were observed in the mass spectrum. When α,α,α′,α′- tetramethyl-2,2′-biphenyldimethanol (16a) was treated under the reaction conditions, the molecule afforded an unstable dialkoxy disulfide that oligomerized. According to MALDI analysis, the sample studied was mainly constituted of 7-unit oligomers. The latter was then further used as a chemical reference for the interpretation of other systems.
27. 1H NMR, this unstable molecule quickly underwent elimination at room temperature to form the corresponding diene. Oligomerization was observed as well during an attempt to isolate the molecule at low temperature. The nature of the effects involved still remains unclear but the synthesis of cyclic dialkoxy disulfides from open chain diols appears difficult to achieve.
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