Rearrangement of the carbanion generated from a tied-back 1,2,4-trithiolane oxide (6,7,8-trithiabicyclo[3.2.1]octane 6-oxide)

Autor:	Kazuyo Umezawa, Juzo Nakayama, Tetsuya Nakaniwa, Akihiko Ishii
Rok vydání:	1999
Předmět:	chemistry.chemical_classification Bicyclic molecule Organic Chemistry Oxide chemistry.chemical_element Salt (chemistry) Biochemistry Medicinal chemistry chemistry.chemical_compound chemistry Deuterium Drug Discovery Thiolactone Organic chemistry Lithium Octane Carbanion
Zdroj:	Tetrahedron. 55:10341-10350
ISSN:	0040-4020
DOI:	10.1016/s0040-4020(99)00589-x
Popis:	Treatment of 2,2,4,4-tetramethyl-6,7,8-trithiabicyclo[3.2.1]octane 6-exo-oxide (3) with LDA, followed by treatment with D2O, RI (R = Me, Et), and 2-PrBr, yielded the deuterated starting compound (3-d), bicyclic 1,3-dithietane oxides (12, 13), and (2-propyldithio)thiolactone (14), respectively. The initially- formed bridgehead lithium salt (11) opens the bicyclic skeleton to give the lithium δ-thioxoperoxydithiocarboxylate (15), which finally isomerizes to the lithium [3-oxo(2-thianyl)]disulfide (19) via the peroxydithiocarboxylate-α-oxodisulfide rearrangement.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::fb9004bba34a706a8d252ec8b2e39494 https://doi.org/10.1016/s0040-4020(99)00589-x Zobrazit plný text záznamu Full Text from ScienceDirect