Abstract
The photochemistry of a phenyl and 1,2-diphenyl substituted sulfite ester is reported. The performance of photoreactions under relatively mild reaction conditions enables the detection of products that have not been observed in previous studies. It is concluded that, complementary to the initially proposed carbene intermediates, diradicals may also be considered.
Highlights
Photoinduced ring-opening or ring-fragmentation processes constitute an important type of reaction in organic photochemistry and have been examined both from a mechanistic and a synthetic point of view [1,2,3,4,5]
To provide further insight into the mechanism of the photoinduced cleavage of the cyclic sulfites, we examined the styrene glycol sulfite (8) and the hydrobenzoin sulfite (9); and we demonstrate that diradical intermediates are generated during the photoextrusion processes
The irradiation of the cyclic sulfite 8 for 3 h in acetonitrile gave phenyl acetaldehyde (3a), bibenzyl (4) and toluene (7) in Scheme 2; in contrast to the results of the photoreaction of the cyclic carbonate ester 1a under similar conditions, the oxirane 2a was not detected as a reaction product
Summary
Photoinduced ring-opening or ring-fragmentation processes constitute an important type of reaction in organic photochemistry and have been examined both from a mechanistic and a synthetic point of view [1,2,3,4,5]. The performance of photoreactions under relatively mild reaction conditions enables the detection of products that have not been observed in previous studies. Griffin et al reported that carbene intermediates are formed upon irradiation of cyclic carbonate esters such as 1b, as evidenced by the interception with appropriate trapping reagents; whereas the formation of persistent primary photoproducts has not been observed
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