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Carbenes And Nitrenes In Organic Chemistry

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4 pages in length. The basic composition of carbenes is such that as electron deficient molecular species, their uncharged state plays an integral role in containing a sextet of electrons that surround a divalent carbon atom. By comparison, nitrenes - uncharged electron deficient molecular species as well - harbor a sextet of electrons that surround a monovalent nitrogen atom. Single state is presented as electrophilic character, trigonal planar geometry, while triple state is diradical-like in nature, linear geometry (Wieder, no date). For nitrene insertion to occur, chiral alkane concentration is separate from observed rotation. Triplet nitrene is formed in greater measure when chiral alkane concentration is under one-hundred percent; this occurs, however, to the detriment of initially produced singlet nitrene. Bibliography lists 4 sources.

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4 pages (~225 words per page)

File: LM1_TLCorgchem.rtf

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By comparison, nitrenes - uncharged electron deficient molecular species as well - harbor a sextet of electrons that surround a monovalent nitrogen atom. Single state is presented as electrophilic character, trigonal planar geometry, while triple state is diradical-like in nature, linear geometry (Wieder, no date). For nitrene insertion to occur, chiral alkane concentration is separate from observed rotation. Triplet nitrene is formed in greater measure when chiral alkane concentration is under one-hundred percent; this occurs, however, to the detriment of initially produced singlet nitrene. As Wieder (no date) duly notes, "the fact that a higher concentration of triplet nitrene does not affect the observed rotation of chiral product is indicative of the inability of the triplet species to insert into alkyl C-H bonds." Nitrenes and carbenes were not always considered a valuable commodity - either individually or as a duo - for synthetic intermediates; rather, half a century ago they were thought of as "curious highly reactive species" (Doyle, 2005, p. 561). At issue were the aspects of reactivity and selectivity; without regioselectivity or streoselectivity, neither the carbene nor nitrene presented as a viable component despite their respective insertion to carbon-hydrogen bonds and addition to carbon-carbon multiple bonds. It was not long, however, until their true worth was discovered in the form of "valued units for organic synthesis" (Doyle, 2005, p. 562). Could they both arise through the same mechanism but differ in the philicity of the metal carbine, or did one proceed through a pathway that was different from the other? The answers came reluctantly over an extended period, but they paved the way to the synthetic uses that we enjoy today (Doyle, 2005, p. 563). The uses of carbene and nitrene are vast and multidisciplinary, encompassing a number of ...

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