Journal of Organic Chemistry p. 261 - 264 (1980)
Update date:2022-08-04
Topics:
Cere, Vanda
Guenzi, Alberto
Pollicino, Salvatore
Sandri, Edda
Fava, Antonino
The concerted fragmentation method of Whitham has been applied to the configurational inversion of cis-thiacyclooct-4-ene (1) to give (35percent overall yield) trans-thiacyclooct-4-ene (2) of >98 percent configurational purity.The required protection of the S atom has been afforded by methylation, while deprotection was achieved by homogeneous LiAlH4 reduction in THF.Some peculiar NMR properties of the 1-methyl and 1-oxide derivatives of trans-thiacyclooctene are reported.
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