Réaction #549811

Équation de réaction

trans-1,2-diacetoxy-1,2-dihydrobenzocyclobutene

rac-3'-acetoxy-3'-acetyl-1',2',3',4',5',8'-hexahydro-5',8'-dioxospiro[1,3-dithiolane-2,1'-naphthalene]

→

rac-3'-acetoxy-3'-acetyl-1',2',3',4',5',12'-hexahydro-5',12'-dioxospiro-[1,3-dithiolane-2,1'-naphthacene]

Rendement 82.0%

Solvants

xylene

Conditions de réaction

Traitement

1. 1
   Températureheated
2. 2
   Températureunder reflux under an atmosphere of nitrogen for 16 hours
3. 3
   AutreThe solution was evaporated to dryness
4. 4
   workup.STIRRINGthe residue was stirred with 20 ml of diethyl ether
5. 5
   Filtrationfiltered

Mode opératoire

A mixture of 0.825 g (0.00375 mol) of trans-1,2-diacetoxy-1,2-dihydrobenzocyclobutene and 1.20 g (0.0034 mol) of rac-3'-acetoxy-3'-acetyl-1',2',3',4',5',8'-hexahydro-5',8'-dioxospiro[1,3-dithiolane-2,1'-naphthalene] [prepared as described in Example 5(A)] in 65 ml of xylene was stirred and heated under reflux under an atmosphere of nitrogen for 16 hours. The solution was evaporated to dryness and the residue was stirred with 20 ml of diethyl ether and filtered to give 1.259 g (82%) of rac-3'-acetoxy-3'-acetyl-1',2',3',4',5',12'-hexahydro-5',12'-dioxospiro-[1,3-dithiolane-2,1'-naphthacene] in the form of a bright yellow solid of melting point 239°-241° C.

Source