Photoisomerization of 9-thiabicyclo[3.3.1]non-6-en-2-one

Padwa, Albert; Battisti, Angelo; Shefter, Eli

doi:10.1021/ja01042a081

Cited by 14 publications

(2 citation statements)

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“…In the fall of 1966, I was offered an Associate Professorship at the State University of New York at Buffalo and decided to return to my native state. At SUNY Buffalo we continued our ongoing photochemical program using a variety of small ring heterocyclic systems and encountered some remarkably interesting photorearrangements along the way . A few of the many systems that were examined are outlined in Scheme .…”

Section: Mechanistic Organic Photochemistry Period (1962−1977)mentioning

confidence: 99%

A Chemistry Cascade: From Physical Organic Studies of Alkoxy Radicals to Alkaloid Synthesis

Padwa

2009

J. Org. Chem.

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In this Perspective, I present a personal account of a succession of chemical projects that I was involved with, each of which triggered or initiated my next research undertaking. It started with my early work in the field of physical organic photochemistry, which, in turn, guided me to my current research dealing with the synthesis of biologically active alkaloids. The article highlights some of the dominant themes of my research program over the past 48 years. Subject matter that is discussed includes the generation of reactive intermediates by photoexcitation, [1,3]-dipolar cycloaddition chemistry, rhodium(II)-catalyzed domino reactions of alpha-diazo carbonyl compounds, intramolecular [4 + 2]-cycloaddition of 2-amidofurans, and the utilization of various thio fragments for the synthesis of nitrogen heterocycles.

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Section: Mechanistic Organic Photochemistry Period (1962−1977)mentioning

confidence: 99%

A Chemistry Cascade: From Physical Organic Studies of Alkoxy Radicals to Alkaloid Synthesis

Padwa

2009

J. Org. Chem.

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“…We therefore turned our attention to the related oxa system in order to make a comparison with the photochemistry of the above ß-keto sulfides. Our initial experiments were involved with the photochemistry of 9oxabicyclo[3.3.1]non-6-en-2-one (9) and 9-oxabicyclo- [3.3.1]non-2-one (10).12 A critical difference between (12) The syntheses of 9 and 10 and their physical properties will be described in our full paper. All new compounds were analyzed by the two systems under consideration is that the oxa system is devoid of an excited-state interaction of the two chromophores (uv (95% ethanol) of 9, 290 µ (e 35); 5, 251 and 304 µ (e 300 and 250)).…”

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confidence: 99%