This Review describes singlet oxygen (1O2) in the organic synthesis of targets on possible 1O2 biosynthetic routes. The visible-light sensitized production of 1O2 is not only useful for synthesis; it is extremely common in nature. This Review is intended to draw a logical link between flow and batch reactions—a combination that leads to the current state of 1O2 in synthesis.

Using Singlet Oxygen to Synthesize Natural Products and Drugs

New Mechanistic and Synthetic Aspects of Singlet Oxygen Chemistry

Tetrahedron report number 149

The Renaissance in Cyclooctatetraene Chemistry

Although various bicyclo[3.3.0]octane derivatives have been known for several decades, the chemistry of this ring system and the higher polyquinanes has developed particularly rapidly in the last decade. These developments have been stimulated by a wide range of interests and have encompassed a broad spectrum of research chemists. One may now safely claim that polyquinanes are readily available molecules. The more complex members of this class, particularly those endowed with all-cis stereo-chemistry, take on a “sphere-like” topology and conformational rigidity. As sphericality increases, the ability of a molecule to exclude solvation from its inner core is enhanced. Can smaller molecules or atoms be occluded therein? And what about completely enclosed structures such as the pentagonal dodecahedrane? What unique properties will characterize compounds of this type? It is the quest for such information that will propel the field of polyquinane chemistry rapidly forward in the years to come. The increasing complexity of natural products having multiply fused cyclopentanoid rings will generate a comparably high level of chemical investigation in this field.

The development of polyquinane chemistry

Electronic control of stereoselectivity. 5. Stereochemistry of singlet oxygen capture by cyclopentadiene rings fused to norbornyl and norbornenyl frameworks

Mećhanistic dichotomy in cycloadditions to cyclooctatetraeneiron tricarbonyl. X-ray crystal structure analysis of the TCNE and CSI adducts

Transition metal catalyzed rearrangement of 11,12-dimethyl[4.4.2]propella-2,4,11-triene as a route to stable cyclooctatetraene bond shift isomers. Implications for [1,5]-sigmatropic migration within the metal coordination sphere

Conformational and stereochemical consequences of uniparticulate electrophilic additions to cis-bicyclo[6.1.0] nonatrienes. Reactions with tetracyanoethylene

Substituent control of regiospecific pathways in di-.pi.-methane photorearrangements which utilize benzo-vinyl bonding schemes

Jon Clardy

Papers

Electronic control of stereoselectivity. 5. Stereochemistry of singlet oxygen capture by cyclopentadiene rings fused to norbornyl and norbornenyl frameworks

Mećhanistic dichotomy in cycloadditions to cyclooctatetraeneiron tricarbonyl. X-ray crystal structure analysis of the TCNE and CSI adducts

Transition metal catalyzed rearrangement of 11,12-dimethyl[4.4.2]propella-2,4,11-triene as a route to stable cyclooctatetraene bond shift isomers. Implications for [1,5]-sigmatropic migration within the metal coordination sphere

Conformational and stereochemical consequences of uniparticulate electrophilic additions to cis-bicyclo[6.1.0] nonatrienes. Reactions with tetracyanoethylene

Substituent control of regiospecific pathways in di-.pi.-methane photorearrangements which utilize benzo-vinyl bonding schemes