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. 2009 Jun 1;74(5):7711-7783.
doi: 10.1135/cccc2008195.

SULFANYLATION OF 1,3-DITHIANE ANIONS BY 5-(ALKYLSULFANYL)-1-PHENYLTETRAZOLES

Venugopal Gudipati  1 , Reena Bajpai, Dennis P Curran
Affiliations

SULFANYLATION OF 1,3-DITHIANE ANIONS BY 5-(ALKYLSULFANYL)-1-PHENYLTETRAZOLES

Venugopal Gudipati et al. Collect Czechoslov Chem Commun. .

Abstract

An unusual reaction between 1,3-dithiane anions and by 5-(alkylsulfanyl)-1-phenyltetrazoles has been discovered in which the dithiane anion formally displaces the 1-phenyltetrazole ring from sulfur to provide a sulfanylated dithiane.

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Figures

Fig.1
Fig.1
Structure of tetrafibricin 1 and high level retrosynthetic analysis
Fig.2
Fig.2
A speculative mechanism for the sulfanylation
Scheme 1
Scheme 1
Synthesis of the precursors 13 and 17 for dithiane alkylation
Scheme 2
Scheme 2
Sulfanylation of dithiane 13 by S-alkyl-N-phenylthioalkyltetrazole 17
Scheme 3
Scheme 3
Simple model sulfanylations
Scheme 4
Scheme 4
Synthesis of alternative C21–C30 fragment 27
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References

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