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   PATERNO-BUCHI reaction




mechanism:


remarks:

  • isc = inter system crossing
  • The oxygen atom of DHF influences regioselectivity.
  • In the excited state, the carbonyl oxygen atom is electrophile.
  • If alkene concentration is high, the reaction occurs before the isc.


example:



references:

Arkivoc 2000, 1, 133.
J. Am. Chem. Soc. 1997, 119, 2437.
J. Org. Chem. 1997, 62, 4900.
Tetrahedron Lett. 1964, 48, 3657.