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1. Structure and Strain . . . . . . . . . . . . . . 2. Spectral Characteristics . . . . . . . . . . . . . 3. The Polarity of Alkylidenecycloproparenes . . . . . . . . Reactions of Cycloproparenes . . . . . . . . . . . . . 1. Substitutions . . . . . . . . . . . . . . . . 2. Addition Reactions . . . . . . . . . . . . . . 3. Rearrangements . . . . . . . . . . . . . . . 4. Reactions with Transition Metal Reagents .

0 ee excess in the hub, as compared to neutral 8. 5 ee. 4. Inversion Barriers in Anionic Species Calculations show that the most interesting feature of corannulene, its curvature, decreases continuously with increasing negative charge. 37/~ for the dianion triplet and tetraanion, respectively. 5s'57 Hence, despite this trend, the tetraanion still prefers the nonplanar conformation. 3 kcal/mol for the tetraanion. 54'55Electron correlation effects increase the barriers significantly to approximately 14, 8-9, and 3 kcal/mol for the neutral, dianion, and tetraanion, respectively.

W. J. Chem. , Chem. Commun. 1994, 2271. CHEMISTRY OF CYCLOPROPARENES Paul M ller 1. 2. 3. 4. Introduction . . . . . . . . . . . . . . . . . . Synthesis of Cycloproparenes . . . . . . . . . . . . . 1. General Strategies . . . . . . . . . . . . . . . 2. Strained, Fused, and Short-Lived Cycloproparenes . . . . . . 3. Heterocyclic and Functionalized Cycloproparenes . . . . . . 4. Alkylidenecycloproparenes . . . . . . . . . . . . Physical Properties .

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