1963
DOI: 10.1021/ic50010a010
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Carboranes. IV. Chemistry of Bis-(1-carboranylalkyl) Ethers

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Cited by 30 publications
(8 citation statements)
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“…A great deal of independent study over the past 30 years has led to the characterization of a C- ortho -carboranyl group as powerfully electron-withdrawing (as opposed to B- ortho -carboranyl groups which are more or less electron-donating, depending on the position of B-substitution). Arguments are based on the high acid strength of carboranyl carboxylic acids,Hammett σ-constant determinations and Taft analysis of 19 F NMR shifts ,, of suitable derivatives, the ease of metalation of the carboranyl C−H group, , the relative lack of reactivity of C-halomethyl carboranes toward nucleophiles, ,, and a host of other observations regarding the reactivity of these species. …”
Section: Resultsmentioning
confidence: 99%
“…A great deal of independent study over the past 30 years has led to the characterization of a C- ortho -carboranyl group as powerfully electron-withdrawing (as opposed to B- ortho -carboranyl groups which are more or less electron-donating, depending on the position of B-substitution). Arguments are based on the high acid strength of carboranyl carboxylic acids,Hammett σ-constant determinations and Taft analysis of 19 F NMR shifts ,, of suitable derivatives, the ease of metalation of the carboranyl C−H group, , the relative lack of reactivity of C-halomethyl carboranes toward nucleophiles, ,, and a host of other observations regarding the reactivity of these species. …”
Section: Resultsmentioning
confidence: 99%
“…Carboranes are known to exist in three (o-, m-, p-) isomeric forms. [1][2][3][4][5][6][7][8][9] Information on the electrophilic properties of carboranes is sparse. Nevertheless, since the hydrogen atoms bonded to o-carborane's two carbon atoms are acidic, the doubly deprotonated di-anion, (C 2 B 10 H 10 ) 2− has been produced by reacting o-carborane with n-butyl-lithium in tetrahydrofuran.…”
Section: Introductionmentioning
confidence: 99%
“…The largest and most consistent set of runs (no. [7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22] in Table I) was made at 0.25 atm, and although the yields are not as high as in later runs at 10 mm, the data reveal some interesting things about the types of reactions that occur. Yield data for the individual closocarborane products are plotted in Figures 3-5, while total yield and per cent conversion are shown in Figure 6.…”
Section: Discussion Of Experimental Resultsmentioning
confidence: 99%