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Advances in Strained and Interesting Organic Molecules, by B. Halton

By B. Halton

The 8th quantity of this sequence includes six chapters and describes various fascinating strained and never so strained molecules and their use - or abuse - within the widest feel. This quantity includes a place precis of planar carbon networks, the sector of strained allenesis addressed via contemplating the 5- to- nine-membered ring derivatives and this is often via an creation to the character of carbene geometry and using ESR spectroscopy in deducing carbene constitution. using strained molecules within the synthesis of vital new compounds of a common and non-natural nature is a prime subject matter within the quantity. different parts which are mentioned are strained carbohydrates, stereocontrolled entry to average items and polymer platforms in addition to a far wanted contribution to the sequence on small-ring nitrogen heterocycles.

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Am. Chem. , 121 (1999) 8182. [70] Wan, W. , Kimball, D. , and Hale),, M. , Tetrabedron Lett, 39 (1998) 6795. [71] Wan, W. , Brand, S. , Pak, J. , and Haley, M. , submitted. [72] Matzger, A. J. and Vollhardt, K. , 39 (1998) 6791. [73] Bunz, U. H. E, Top. Curt. , 201 (1999) 131. Planar Carbon Networks 41 [74] Bunz, U. H. , Angew. , Int. Ed. , 32 (1993) 1653. [75] Bunz, U. H. , Organometallics, 13 (1994) 3823. , and Bunz, U. H. E, J. Am. Chem. , 119 (1997) 1472. , Knobler, C. , and Diederich, E, Angew.

PC h >450 nm 30a, R=H 30h, R=Ph 3 la, R=H 311~ R=Ph Ph Ph MeLi Br 33 32a, R=H 321~ R=Ph 0~ 31a Scheme 7. H Strained Cyclic Allenes 49 h Ti-IF 20% H3C" "CH3 35 H3C ~ "CH3 36 + 37 -t Ph Ph H3 38 39 H: Scheme 8. Cyclohexa-1,2,4-triene (41) reacts exclusively at the conjugated allene ~ bond in the [2+4] cycloaddition and this has been explained by the more favorable frontier orbital energies in comparison to those of the nonconjugated allene rt bond. However, the selectivity of 44 needs to be confirmed by further investigations.

An interesting feature of these trapping experiments was the observation of different chemoselectivity. [2+4] Cycloaddition reactions with the allene take place exclusively at the double bond most remote from the oxygen atom, whereas [2+2] cycloaddition reactions prefer the enol ether double bond. In the case of the [2+4] cycloaddition reaction the electron-pure double bond, which is that more remote from the oxygen atom, will react preferentially with electron-rich dienes. For the formation of the [2+2] cycloaddition products a two-step mechanism involving diradical intermediates was suggested [42,43].

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