We have designed a new photoremovable protecting group 1  that releases alcohols in high quantum yields. The photorelease of the alcohol takes place in argon and oxygen saturated solutions. We elucidated the mechanism for photorelease using product studies, transient spectroscopy and molecular modeling. Upon irradiation 1  undergoes intramolecular hydrogen abstraction to form biradical 2 . Biradical 2  expels a nitrogen molecule to form imine radical 3  that results in formation of 4  and release of the alcohol moiety. In completion to biradical 2 expelling a nitrogen molecule, it also undergoes intersystem crossing to form Z- photoenol 3 . The high yields for the photorelease are due to the fact the imine radical 3  cannot regenerate the starting material as photoenols5 . 

Synthetically modified photoremovable protecting group to achieve high yield photorelease of alcohol

245th National Meeting (2013)

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