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Norrish Type I Reaction

(Norrish Type I Process, Norrish Type I Cleavage)

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr464

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Norrish Type I Reaction. Comprehensive Organic Name Reactions and Reagents. 464:2062–2066.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

The light-initiated carbon-carbon bond cleavage between the α-carbon and the carbonyl of a ketone or an aldehyde to form an alkyl and an acyl radical pairs, from which a variety of products can be formed, such as alkane, alkene, cyclic acetal, decarbonyl compound, and oxetane and this reaction is referred to as the Norrish type I reaction. This reaction is initiated by a n-π* excitation followed by an α-cleavage to form an acyl and an alkyl radical pairs. It has been reported that this reaction is influenced by both the structure of the substrate and the reaction conditions, as evidenced in the different product distributions between the reactions in the gas phase and in the solution phase. The aliphatic cyclic imides and small cyclic ketones up to cycloheptanone undergo only the Norrish type I reaction from both singlet and triplet excited states, whereas acetophenone and benzophenone are often used as the Norrish type I photosensitizers. This reaction in the presence of zeolite and cyclodextrin and in the solid state produces good results. This reaction has been used extensively in organic synthesis and photochemistry.

Keywords:

  • oxetane;
  • cage effect;
  • cycloheptanone;
  • zeolite