126797-78-2

Upstream product

• 111-29-5 1 ,5-pentanediol 
• 41323-59-5 5-Hydroxyhept-6-ene-1,5-diol 
• 136547-59-6 O-4-formylbutyl O-phenyl thionocarbonate 
• 136547-53-0 Thiocarbonic acid O-(5-hydroxy-pentyl) ester O-phenyl ester 
• 126797-71-5 O-(5-Hydroxy-6-heptenyl) O-phenyl thionocarbonate 
• 594-19-4 tert.-butyl lithium 
• 100-39-0 benzyl bromide 
• 126824-84-8 (Z)-7,8,9,10-Tetrahydro-4H-1,3-oxathiecin-2-one 

Relevant academic research and scientific papers

[3,3]Sigmatropic ring expansion of cyclic thionocarbonates. IV. Relationship between ring size of cyclic thionocarbonates and geometry of created double bond in medium- and large-membered thiolcarbonate

Medium- and large-membered cyclic thiolcarbonates containing an (E)- or (Z)-double bond were synthesized by two methods using [3,3]sigmatropic ring expansion of cyclic thionocarbonates. The [3,3]sigmatropic ring expansion proceeds exclusively via the transition state bearing the chain tethered in a cis relationship when the cyclic thionocarbonates are 8-membered or smaller. Importantly, the ring of the cyclic thionocarbonates determines the double bond geometry of the thiolcarbonate. Conversion of the cyclic thiolcarbonates into (E)- or (Z)-allylic sulfides is also described.

NEW ROUTE TO (Z)-ALLYLIC SULFIDES VIA A 10-MEMBERED THIOLCARBONATE

A new synthesis of a 10-membered thiolcarbonate containing a (Z)-double bond and its conversion into (Z)-allylic sulfides are described.KEYWORDS (Z)-allylic sulfides; 10-membered thiolcarbonate; sigmatropic rearrangement; thionocarbonate