131141-38-3

Upstream product

• 94417-52-4 (Bis-methylselanyl-methyl)-benzene 
• 762-72-1 allyl-trimethyl-silane 
• 24850-33-7 allyltributylstanane 
• 153992-06-4 (Methoxy-methylselanyl-methyl)-benzene 

Relevant academic research and scientific papers

Lewis Acid Activated Reactions of Mixed (O,Se) Acetals with Allyltrimethylsilane and Allyltributylstannane

On the basis of preferential complexation of oxygen or selenium atoms by different Lewis acids, it was expected that, depending on the Lewis acid employed, the title reactions would lead to selective formation of homoallyl ethers or homoallyl selenides.This has not been confirmed by experiment: in almost all the reactions tried homoallyl ethers largely predominated, or were the exclusive allylation products, even when strongly oxygenophilic Lewis acids such as TiCl4 were used.In the cases of the latter type of Lewis acids, the results observed with (O,Se) and a couple of (O, S) mixed acetals are interpreted in terms of two major factors operating in opposite directions. 1H NMR data of a mixture of TiCl4 and (O,Se) acetal indicate that preferential (but not exclusive) complexation of the oxygen moiety takes place indeed.However, because of the much stronger C-O bond as compared to the C-Se bond, this latter (also activated by the Lewis acid to some extent) undergoes cleavage by allyl metals to give homoallyl ethers as predominating products.In contrast with BF3*OEt2, boron trichloride and boron tribromide were found to react with (O, Se) acetals to give the corresponding α-halo selenides, which in turn were cleanly transformed into homoallyl selenides on reaction with allyltrimethylsilane in the presence of tin tetrachloride.

LEWIS ACID MEDIATED REACTION OF SELENOACETALS WITH ALLYLSILANES AND ALLYLSTANNANES: SYNTHESIS OF HOMOALLYLSELENIDES

Selenoacetals react with allyltrimethylsilane in the presence of tin tetrachloride to produce homoallyl selenides in moderate to good yields.Aliphatic acetals react less efficiently than do aromatic ones, especially when steric factors can play a signific

The reaction of allyltrimethylsilane with selenium-stabilized carbon electrophiles

Lewis acid activation of bis(methylseleno)alcanes makes them react with allylsilane to produce the corresponding homoallyl selenides in moderate to good yields, depending on the structure of the starting selenoacetals.