2,3-Sigmatropic rearrangement of sulfonium ylides generated by addition of samarium carbenoids

Synlett

Volumn , Issue 12, 1998, Pages 1366-1368

  Kunishima, Munetaka ^a   Nakata, Daisuke ^a   Goto, Chikako ^a   Hioki, Kazuhito ^a   Tani, Shohei ^a  

^a KOBE GAKUIN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002241616     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1979     Document Type: Article

References (24)

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21. 16S calcd 192.0973, found 192.0956.
22. Though 1,3-dienes could not be isolated due to their low boiling point, the formation of methyl aryl sulfides, another product formed by elimination, could be detected.
23. 2 (4 eq) at rt where 79% of 5 was obtained without treatment of acetaldehyde. The yield of 5 was found to be 82%.
24. 2 in the presence of water resulted in recovery of 1 (87%) with no detectable amount of the sulfonium salt (5). A further attempt using diphenyl sulfide, which was employed to avoid rearrangement of sulfonium ylides, under the same conditions was unsuccessful.