Reactions of sterically congested 1,6- and 1,7-bis(diazo)alkanes with elemental sulfur and selenium: Formation of cyclohexene, 1,2-dithiocane, 1,2-diselenocane, and 1,2,3-triselenecane derivatives

Autor:	Ken Furusawa, Takenori Omata, Juzo Nakayama, Akihiko Ishii
Rok vydání:	2002
Předmět:	Steric effects chemistry.chemical_compound chemistry Yield (chemistry) Heteroatom Cyclohexene chemistry.chemical_element Diazo General Chemistry Medicinal chemistry Sulfur Selenium
Zdroj:	Heteroatom Chemistry. 13:351-356
ISSN:	1098-1071 1042-7163
DOI:	10.1002/hc.10046
Popis:	The reaction of 3,8-bis(diazo)-2,2,4,4,7,7,9,9-octamethyldecane (5) with elemental selenium in 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) at 130°C yielded 1,2-di-tert-butyl-3,3,6,6-tetramethylcyclohexene (1) (64%) and trans-3,8-di-tert-butyl-4,4,7,7-tetramethyl-1,2-diselenocane (8) (13%), while that of 5 with elemental sulfur in DBU gave trans-3, 8-di-tert-butyl-4,4,7,7-tetramethyl-1,2-dithiocane (9) (77%). The reaction of 3,9-bis(diazo)-2,2,4,4,8,8,10,10-octamethylundecane (6) with elemental selenium in DBU at 80°C gave a cyclic triselenide, cis-4,10-di-tert-butyl-5,5,9,9-tetramethyl-1,2,3-triselenecane (11), in 15% yield as the only identifiable product. The structures of 9 and 11 were confirmed by X-ray crystallography. © 2002 Wiley Periodicals, Inc. Heteroatom Chem 13:351–356, 2002; Published online in Wiley Interscience (www.interscience.wiley.com). DOI 10.1002/hc.10046
Databáze:	OpenAIRE
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