TY - CHAP
T1 - Applications of Di-π-Methane and Related Rearrangement Reactions in Chemical Synthesis
AU - Banwell, Martin G.
AU - Bon, David J.Y.D.
N1 - Publisher Copyright:
© 2015 John Wiley & Sons, Inc.
PY - 2015/10/12
Y1 - 2015/10/12
N2 - The di-π-methane (DPM) rearrangement reaction is one of the most studied photochemical transformations. The oxa-di-π-methane (ODPM) rearrangement reaction has been recognized as a powerful synthetic protocol and one that can be applied to both cyclic and acyclic substrates. In the case of aza-di-π-methane (ADPM) rearrangement reactions involving 1-aza-1,4-dienes, regioselective conversions have been observed. The DPM reaction usually takes place through a singlet pathway (S1) in the excited state when acyclic 1,4-dienes are involved. The DPM rearrangement reaction requires a substrate incorporating two olefinic residues (π-systems) linked to a common sp3-hybridized carbon or, in other words, a 1,4-diene. A range of methods is available for the synthesis of the acyclic 1,4-dienes required as substrates for the DPM rearrangement reaction, and some of these are also summarized in the chapter.
AB - The di-π-methane (DPM) rearrangement reaction is one of the most studied photochemical transformations. The oxa-di-π-methane (ODPM) rearrangement reaction has been recognized as a powerful synthetic protocol and one that can be applied to both cyclic and acyclic substrates. In the case of aza-di-π-methane (ADPM) rearrangement reactions involving 1-aza-1,4-dienes, regioselective conversions have been observed. The DPM reaction usually takes place through a singlet pathway (S1) in the excited state when acyclic 1,4-dienes are involved. The DPM rearrangement reaction requires a substrate incorporating two olefinic residues (π-systems) linked to a common sp3-hybridized carbon or, in other words, a 1,4-diene. A range of methods is available for the synthesis of the acyclic 1,4-dienes required as substrates for the DPM rearrangement reaction, and some of these are also summarized in the chapter.
KW - ADPM rearrangement reactions
KW - Chemical synthesis
KW - Cyclic substrates
KW - Di-π-methane rearrangement reactions
KW - ODPM rearrangement reactions
KW - Regioselectivity
UR - http://www.scopus.com/inward/record.url?scp=84960088285&partnerID=8YFLogxK
U2 - 10.1002/9781118939901.ch9
DO - 10.1002/9781118939901.ch9
M3 - Chapter
SN - 9781118347966
SP - 261
EP - 288
BT - Molecular Rearrangements in Organic Synthesis
PB - Wiley
ER -