I actually did a literature search and 2 refs came up. This synthesis one, and the one you posted Rhodium.
In the article the cleave a bunch of ethers and note that "It was found that the use of iodotrichlorosilane is compatible with compounds containing double bonds..."
Yields were between 11% - 80%.
R
2 = OCH
3 R
4 = H
2C:CH-CH
2-
Method B: 67% yield, 20 h relux.
Edit Oops, i left out the better example
![Embarrassed :-[](https://thevespiary.org/talk/Smileys/default/embarrassed.gif)
a bit distracted sorry.
R
1 = OH
R
2 = OCH
3R
4 = H
2C:CH-CH
2-
Method B: 62% yield, 20 h reflux
Note: the silicon tetrachloride and iodide salt is forming iodotrichlorosilane.
Cleavage of ethers with silicon tetrachloride/sodium iodide; typical proceedures:Method A: Allyl phenyl ether (2.68 g, 20 mmol) and sodium iodide (3.3 g, 22 mmol) are dissolved in 1:1 dichloromethane/acetonitrile (20 mL). Silicon tetrachloride (2.5 mL, 22 mmol) is added from a dry syringe and the mixture is stirred and heated under reflux for 8 h. The mixture is then hydrolysed by pouring into water (50 mL) and extracted with ether (2 x 50 mL). The phenol is extracted from the ether layer with 10% sodium hydroxide solution (20 mL), the extract is acidified, and extracted with ether. The ether is evapourated and the phenol obtained by distillation of the residue; yield: 1.56 g (84%); one spot on TLC (silica gel, 1:3 ethyl acetate/hexane).
Method B; o-Dimethoxybenzene (2.76 g, 20 mmol) and sodium iodide (6.6 g, 44 mmol) are added to 1:1 acetonitrile/toluene (30 mL). Silicon tetrachloride (5 mL, 44 mmol) is added and the mixture is stirred and heated under relfux for 12 h. Catechol is isolated from the reaction mixture as described in method A.
SiCl
4 is not OTC, but the yields are at least resonable. Has this not been discussed before?
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