Photochemical reactions of sulfide-containing alkyl phenylglyoxylates

Add time:08/02/2019    Source:sciencedirect.com

Ethylthioalkyl phenylglyoxylates (2) underwent regioselective photocyclization to produce up to 13-membered ring thiacyclols (3) in good yields. Cyclization occurred between the excited carbonyl group and the carbon a to the sulfur on the remote side. The more methylenes placed between the carbonyl group and the sulfide, the lower the yield of 3 while intermolecular hydrogen abstraction induced reductive dimerization and intramolecular Norrish Type II photolysis become competitive. The remote cyclization can be rationalized by a photoinduced electron transfer from the sulfur atom to the excited carbonyl group followed by proton transfer and subsequent cyclization of the resulting biradical. Rate constants for electron transfer increase as the chain connecting the electron donor and acceptor becomes longer and more flexible.

We also recommend Trading Suppliers and Manufacturers of N-DECYL ETHYL SULFIDE (cas 19313-61-2). Pls Click Website Link as below: cas 19313-61-2 suppliers

Prev:Investigation of steric and electronic effects in the copper-catalysed asymmetric oxidation of sulfides
Next:Efficient Swern oxidation and Corey–Kim oxidation with ion-supported methyl sulfoxides and methyl sulfides)