Research output: Thesis › Doctoral Thesis
Research output: Thesis › Doctoral Thesis
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TY - BOOK
T1 - 4-π-Photocyclisation of Troponoids – Scope and Applications
AU - Lowe, Jack
PY - 2023/8/25
Y1 - 2023/8/25
N2 - This thesis describes the synthesis of novel [3.2.0]bicycles via 4-π-photocyclisation of tropone and its 2-substituted derivatives.Chapter 1 provides a bibliographic overview of the literature pertaining to the synthesis of cyclobutenes, with a particular emphasis on the 4-π-photocyclisation of cyclic 1,3-butadienes.Chapter 2 investigates the optimisation and gram-scale synthesis of phototropone via 4-π-photocyclisation of tropone·BF3 in a batch photoreactor. The phototropone product obtained was subjected to a wide variety of reactions to yield novel small- molecule building blocks.Chapter 3 describes the synthesis of 2-substituted tropones by known litera- ture procedures as well as custom syntheses. The 2-substituted tropones obtained were irradiated both in the presence and absence of BF3·OEt2 to obtain a series of novel [3.2.0]bicycles, and valuable insights into the substituent effects on this reaction were gleaned.Chapter 4 provides overall conclusions from Chapters 2 and 3, as well as ideas for potential future work.Chapter 5 describes the experimental details and characterisation of novel com- pounds described in this thesis.
AB - This thesis describes the synthesis of novel [3.2.0]bicycles via 4-π-photocyclisation of tropone and its 2-substituted derivatives.Chapter 1 provides a bibliographic overview of the literature pertaining to the synthesis of cyclobutenes, with a particular emphasis on the 4-π-photocyclisation of cyclic 1,3-butadienes.Chapter 2 investigates the optimisation and gram-scale synthesis of phototropone via 4-π-photocyclisation of tropone·BF3 in a batch photoreactor. The phototropone product obtained was subjected to a wide variety of reactions to yield novel small- molecule building blocks.Chapter 3 describes the synthesis of 2-substituted tropones by known litera- ture procedures as well as custom syntheses. The 2-substituted tropones obtained were irradiated both in the presence and absence of BF3·OEt2 to obtain a series of novel [3.2.0]bicycles, and valuable insights into the substituent effects on this reaction were gleaned.Chapter 4 provides overall conclusions from Chapters 2 and 3, as well as ideas for potential future work.Chapter 5 describes the experimental details and characterisation of novel com- pounds described in this thesis.
U2 - 10.17635/lancaster/thesis/2098
DO - 10.17635/lancaster/thesis/2098
M3 - Doctoral Thesis
PB - Lancaster University
ER -