Frontier Orbitals: A Practical Manual

Frontier Orbitals: A Practical Manual

Volumn , Issue , 2007, Pages 1-287

  Anh, Nguyên Trong ^a  

^a ECOLE POLYTECHNIQUE   (France)

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EID: 84961985231     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9780470065709     Document Type: Book

References (690)

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3. The validity of these approximations is discussed in Anh N. T., Introduction à la Chimie Moléculaire, Ellipses, Paris, 1994, p. 200.
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82. Alkynes are generally more reactive toward nucleophiles and less reactive toward electrophiles than their alkene counterparts. Strozier R. W., Caramella P., Houk K. N., J. Am. Chem. Soc., 1979, 101, 1340 and references therein.
83. -1 for acetylene and ethylene, respectively.
84. Maurel F., Thesis, University of Paris VI, 1995.
85. Yates K., Schmid G. H., Regulski T. W., Garratt D. G., Leung H.-W., McDonald R., J. Am. Chem. Soc., 1973, 95, 160.
86. Yamataka H., Nagase S., Ando T., Hanafusa T., J. Am. Chem. Soc., 1986, 108, 601.
87. Hyatt J. A., Raynolds P. W., Org. React., 1994, 45, 159.
88. Wang X. B., Houk K. N., J. Am. Chem. Soc., 1990, 112, 1754.
89. Sordo J. A., González J., Sordo T. L., J. Am. Chem. Soc., 1992, 114, 6249.
90. Woodward R. B., Sondheimer F., Taub D., Heusler K., McLamore W. M., J. Am. Chem. Soc., 1952, 74, 4223.
91. In these Hückel calculations, 27a the intramolecular distance is presumed to be the same for each transition state. Therefore, the atomic overlaps are identical and the Pij values are proportional to the frontier orbital coefficients.
92. Houk K. N., Loncharich R. J., Blake J. F., Jorgensen W. L., J. Am. Chem. Soc., 1989, 111, 9172
93. Jorgensen W. L., Lim D., Blake J. F., J. Am. Chem. Soc., 1993, 115, 1936.
94. Hartke K., Phosphorus, Sulfur, and Silicon, 1991, 58, 224.
95. Anh N. T., Canadell E., Eisenstein O., Tetrahedron, 1978, 34, 2283.
96. For a completely different approach, see: Fujimoto H., Inagaki S., Fukui K., J. Am. Chem. Soc., 1976, 98, 2670
97. Fujimoto H., Sugiyama T., J. Am. Chem. Soc., 1977, 99, 15.
98. Nomura Y., Kimura M., Takeuchi Y., Tomodo S., Chem. Lett., 1978, 267
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101. Gonzalez J., Houk K. N., J. Org. Chem., 1992, 57, 3031.
102. Trione C., Toledo L. M., Kuduk S. D., Fowler F. W., Grierson D. S., J. Org. Chem., 1993, 58, 2075.
103. Boger D. L., Tetrahedron, 1983, 39, 2869
104. Boger D. L., Weinreb S. N., Hetero Diels-Alder Methodology in Organic Synthesis, Academic Press, San Diego, 1987.
105. Serckx-Poncin B., Hesbain-Frisque A. M., Ghosez L., Tetrahedron Lett., 1982, 3261.
106. Teng M., Fowler F. W., J. Org. Chem., 1990, 55, 5646 and references therein
107. Boger D. L., Corbett W. L., J. Org. Chem., 1993, 58, 2068 and references cited therein.
108. Boger D.L Corbett W.L; Curran T.T; Kasper A.M; J Am.Chem. Soc; 1991, 113, 1713.
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110. Bertran J., Carbo R., Moret T., Ann. Quim., 1971, 67, 489.
111. Eisenstein O., Lefour J. M., Anh N. T., Chem. Commun., 1971, 969
112. Eisenstein O., Lefour J. M., Anh N. T., Hudson R. F., Tetrahedron, 1977, 33, 523.
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114. Minot C., Anh N. T., Tetrahedron, 1977, 33, 533.
115. This rule should be applied cautiously if the competitive sites belong to different rows of the periodic table (e.g. C versus S. See Exercise 2, p. 92, and Exercise 3, p. 93).
116. However, the application of FO criteria to photochemical reactions is much more difficult because it is often necessary to superimpose different electronic configurations to obtain a realistic excited state model. See also p. 233.
117. Bastide J., Henri-Rousseau O., Bull. Soc. Chim. Fr., 1973, 2290
118. Houk K. N., Sims J., Watts C. R., Luskus L. J., J. Am. Chem. Soc., 1973, 95, 7301
119. Houk K. N., Sims J., Duke R. E. Jr, Strozier R. W., George J. K., J. Am. Chem. Soc., 1973, 95, 7287
120. Minato T., Yamabe S., Inagaki S., Fujimoto H., Fukui K., Bull. Chem. Soc. Jpn., 1974, 47, 1619.
121. Burke L. A., J. Org. Chem., 1985, 50, 3149
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123. Loncharich R. J., Brown F. K., Houk K. N., J. Org. Chem., 1989, 54, 1129
124. Valenti E., Pericàs M. A., Moyano A., J. Org. Chem., 1990, 55, 3582 (AM1 calculations)
125. Birney D. M., Houk K. N., J. Am. Chem. Soc., 1990, 112, 4127
126. Gonzalez J., Houk K. N., J. Org. Chem., 1992, 57, 3031
127. Singleton D. A., Leung S. W., J. Org. Chem., 1992, 57, 4796
128. Brown F. K., Singh U. C., Kollman P. A., Raimondi L., Houk K. N., Bock C. W., J. Org. Chem., 1992, 57, 4862
129. Bachrach S. M., Liu M., J. Org. Chem., 1992, 57, 6736
130. Dâu M. E. T. H., Flament J. P., Lefour J. M., Riche C., Grierson D. S., Tetrahedron Lett., 1992, 33, 2343
131. Cioslowski J., Sauer J., Hetzenegger J., Karcher T., Hierstetter T., J. Am. Chem. Soc., 1993, 115, 1353
132. Jorgensen W. L., Lim D., Blake J. F., J. Am. Chem. Soc., 1993, 115, 2936
133. McCarrick M. A., Wu Y. -D., Houk K. N., J. Org. Chem., 1993, 58, 3330.
134. Vedejs E., Perry D. A., Rondan N. G., J. Am. Chem. Soc., 1983, 105, 7001.
135. Pradère J. P., Bouet G., Quiniou H., Tetrahedron Lett., 1972, 3471.
136. Pradère J.P., N'Guessan Y.T., Quiniou H., Tonnard F., Tetrahedron, 1975, 31, 3059.
137. Guémas J. P., Quiniou H., Sulfur Lett., 1984, 2, 121.
138. Corey E. J., Cheng X.-M., The Logic of Chemical Synthesis, J. Wiley & Sons, N.Y., 1989, p. 19.
139. Corey E. J., Snyder B.B., J. Am Chem. Soc., 1972, 94, 2549.
140. -1)). The positive charge is transferred from a hydrogen to a carbon center. Relevant ionization potentials: H(1s) ≤ 13.6 eV, C(2p) ≤ 11.4 eV.
141. Libit L., Hoffmann R., J. Am. Chem. Soc., 1974, 96, 1370.
142. Pearson R. G., J. Chem. Educ., 1987, 64, 561
143. Ho T. L., Tetrahedron, 1985, 41, 1
144. Ho T. L., Hard and Soft Acids and Bases Principle in Organic Chemistry, Academic Press, New York, 1977.
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146. Huheey J. E., Inorganic Chemistry, 3rd Edn, Harper & Row, New York, 1983, p. A37.
147. Carey F. A., Sundberg R. J., Advanced Organic Chemistry, Plenum/Rosetta, New York, 1977, Part B, p. 16.
148. Kurts A. L., Genkina N. K., Masias A., Beletskaya I. P., Reutov O. A., Tetrahedron, 1971, 27, 4777
149. Sarthou P., Guibé F., Bram G., Chem. Commun., 1974, 377
150. LeNoble W. J., Morris H. F., J. Org. Chem., 1969, 34, 1969
151. LeNoble W. J., Puerta J. E., Tetrahedron Lett., 1966, 1087
152. Brieger G., Pelletier W. M., Tetrahedron Lett., 1965, 3555.
153. Houk K. N., Paddon-Row M. N., J. Am. Chem. Soc., 1986, 108, 2659
154. Sanchez Marcos E., Maraver J., Anguiano J., Bertran J., J. Chim. Phys., 1987, 84, 765.
155. Onsager L., J. Am. Chem. Soc., 1936, 56, 1486.
156. Maurel F., unpublished results.
157. Jones M. E., Kass S. R., Filley J., Barkley R. M., Ellison G. B., J. Am. Chem. Soc., 1985, 107, 109.
158. More than 30 orders of magnitude greater than the force of gravity. Feynman calculates that two grains of sand of 1 mm diameter separated by 30 m would exert a force of 3 million tons on each other if they were completely ionized.
159. Faigle J. F. G., Isolani P. C., Riveros J. M., J. Am. Chem. Soc., 1976, 98, 2049
160. Comisarow M., Can. J. Chem., 1977, 55, 171
161. Fukuda E. K., McIver R. T. Jr, J. Am. Chem. Soc., 1979, 101, 2498
162. Bohme D. K., Mackay G. I., Tanner S. D., J. Am. Chem. Soc., 1980, 102, 407
163. Caldwell G., Rozeboom M. D., Kiplinger J. F., Bartmess J. E., J. Am. Chem. Soc., 1984, 106, 809
164. Johlman C. L., Wilkins C. L., J. Am. Chem. Soc., 1985, 107, 327.
165. Metzner P., Thuillier A., Sulfur Reagents in Organic Synthesis, Academic Press, San Diego, 1994.
166. Schaumann E., in The Chemistry of Double-bonded Functional Groups, Patai S. (Ed.), John Wiley & Sons. Ltd, Chichester, 1989, p. 1324
167. Duus F., in Comprehensive Organic Reactions, Barton D. H. R., Ollis W. D., Neville Jones D. (Eds.), Pergamon Press, Oxford, 1979, Vol. 3, p. 395.
168. Meyers A. I., Tait A., Comins D. L., Tetrahedron Lett., 1978, 4657
169. Beslin P., Vallée Y., Tetrahedron, 1985, 41, 2691.
170. Schuijl P. J. W., Brandsma L., Arens J. F., Recl. Trav. Chim. Pays-Bas, 1966, 85, 1263
171. Beiner J. M., Thuillier A., C. R. Acad. Sci. Paris, Sér. C, 1972, 274, 642.
172. In 'normal' transition states, the incipient bond has ~1.4 as its equilibrium value (Anh N. T., Maurel F., Lefour J. M., New J. Chem., 1995, 19, 353 and references cited therein). We can then take as first 'guesstimates' 2.55 Å for the (Electrophile...S) distance in thiophilic transition states and 2.16 Å for the (E...C) distance in carbophilic transition states. The latter transition states are thus tighter and later than the former transition states.
173. Berrada S., Metzner P., Rakotonirina R., Bull. Soc. Chim. Fr., 1985, 881.
174. Metzner P., in Review on Heteroatom Chemistry, Oae S. (Ed.), MYU, Tokyo, 1989, Vol. 2, p. 152.
175. Léger L., Saquet M., Bull. Soc Chim. Fr., 1975, 657
176. Meyers A. I., Tait T. A., Comins D. L., Tetrahedron Lett., 1978, 4657.
177. Hartke K., Gillmann T., Liebigs Ann. Chem., 1986, 1718.
178. Narashiman L., Sanitra R., Ramachandran J., Sastry V. V. S. K., Chem. Commun., 1978, 719.
179. Beak P., Yamamoto J., Upton C. J., J. Org. Chem., 1975, 40, 3052
180. Tominaga Y., Kohra S., Hosomi A., Tetrahedron Lett., 1987, 28, 1529.
181. There are no AM1 parameters for Li and Na.
182. Duval D., Géribaldi S., in The Chemistry of Enones, Patai S., Rappoport Z. (Eds), John Wiley & Sons, Ltd, Chichester, 1989, Part I, p. 355
183. Perlmutter P., Conjugate Addition Reactions in Organic Synthesis, Pergamon Press, Oxford, 1992.
184. Kohler E. P., Am. Chem. J., 1907, 38, 511.
185. Gilman H., Kirby R. H., J. Am. Chem. Soc., 1941, 63, 2046.
186. Eisenstein O., Lefour J. M., Minot C., Anh N. T., Soussan G., C. R. Acad. Sci. Paris, Série C, 1972, 274, 1310
187. Bottin J., Eisenstein O., Minot C., Anh N. T., Tetrahedron Lett., 1972, 3015
188. Deschamps B., Anh N. T., Seyden-Penne J., Tetrahedron Lett., 1973, 527
189. Durand J., Anh N. T., Huet J., Tetrahedron Lett., 1974, 2397
190. Barbot F., Chan C. H., Miginiac P., Tetrahedron Lett., 1976, 2309
191. Cossentini M., Deschamps B., Anh N. T., Seyden-Penne J., Tetrahedron, 1977, 33, 409
192. Priesta W., West R., J. Am. Chem. Soc., 1976, 98, 8421
193. Seyferth D., Murphy G. J., Mauzé B., J. Am. Chem. Soc., 1977, 99, 5317.
194. Loupy A., Seyden J., Tetrahedron Lett., 1978, 2571.
195. I thank é. Bézard for drawing my attention to this point.
196. Danishefsky S., Kerwin J. F. Jr, J. Org. Chem., 1982, 47, 3183. For a cycloaddition with acrylo-nitrile
197. Janz G. J., Duncan N. E., J. Am. Chem. Soc., 1953, 75, 5389.
198. Deschamps B., Tetrahedron, 1978, 34, 2009, and references therein.
199. Seguin J. R., Beaupere D., Bauer P., Uzan R., Bull. Soc. Chim. Fr., 1974, 167.
200. Lefour J. M., Loupy A., Tetrahedron, 1978, 34, 2597.
201. Four species are present in the reaction mixture: the nucleophile and the carbonyl, each either naked or associated with the cation. As the equilibrium will be displaced constantly, the reaction occurs between the most reactive species: the naked nucleophile and the complexed carbonyl.
202. This prediction contradicts HSAB theory.
203. Bertrand J., Gorrichon L., Maroni P., Meyer R., Tetrahedron Lett., 1982, 23, 3267.
204. Kyriakou G., Roux-Schmitt M. C., Seyden-Penne J., Tetrahedron, 1975, 31, 1883
205. Deschamps B., Seyden-Penne J., Tetrahedron, 1977, 33, 413
206. Wartski L., El-Bouz M., Seyden-Penne J., Dumont W., Krief A., Tetrahedron Lett., 1979, 1543
207. Wartski L., El-Bouz M., Seyden-Penne J., J. Organomet. Chem., 1979, 177, 17 and reference cited therein See also ref. 48.
208. Croisat D., Seyden-Penne J., Strzalko T., Wartski L., Corset J., Froment F., J. Org. Chem., 1992, 57, 6435
209. Strzalko T., Seyden-Penne J., Wartski L., Froment F., Corset J., Tetrahedron Lett., 1994, 35, 3935
210. Strzalko T., Seyden-Penne J., Wartski L., Corset J., Castella-Ventura M., Froment F., J. Org. Chem., 1998, 63, 3295
211. Corset J., Castella-Ventura M., Froment F., Strzalko T., Wartski L., J. Org. Chem., 2003, 68, 3902.
212. Seguin J. R., Beaupere D., Bauer P., Uzan R., Bull. Soc. Chim. Fr., 1974, 167.
213. Configuration interaction (CI) is the MO equivalent of valence bond theory's resonance. The difference is that we combine limiting electronic configurations rather than limiting formulae. Electrons revolving around the nucleus are often compared to men circling around a beautiful woman. In Hückel calculations, no man pays any attention to any other man (independent electrons), which is not very realistic. Hartree-Fock (HF) calculations take into account the average repulsion: the rivals tend to avoid one another. CI is a simple way to depict the instantaneous correlation. It underlines the fact that at each instant, every man tries to keep the greatest distance between himself and each of his rivals.
214. See p. 145 for the definitions of '6-endo' and '5-exo'.
215. Leach A. G., Wang R., Wohlhieter G. E., Khan S. I., Jung M. E., Houk K. N., J. Am. Chem. Soc., 2003, 125, 4271.
216. Fujimoto H., Yamabe S., Minato T., Fukui K., J. Am. Chem. Soc., 1972, 94, 9205
217. Fleming I., Frontier Orbitals and Organic Chemical Reactions, John Wiley & Sons, Inc., New York, 1976
218. Fossey J., Lefort D., Sorba J., Les Radicaux Libres en Chimie Organique, Masson, Paris, 1993.
219. Fossey J., Thesis, Paris, 1974.
220. Poblet J. M., Canadell E., Sordo T., Can. J. Chem., 1983, 61, 2068.
221. Houk K. N., Luskus L. J., Bhacca N. S., J. Am. Chem. Soc., 1970, 92, 6392.
222. Paddon-Row M. N., Aust. J. Chem., 1974, 27, 299.
223. Houk K. N., George J. K., Duke R. E. Jr, Tetrahedron, 1974, 30, 523.
224. As the number of conjugated atoms increases, the energy gaps between the MOs decrease.
225. For example, reactions which have been treated by MNDO and PM3 methods include: Cheney B. V., J. Org. Chem., 1994, 59, 773
226. Matsuoka T., Harano K., Hisano T., Heterocycles, 1994, 37, 257. I have been unable to reproduce the experimental results using Hückel calculations.
227. A subjacent lone pair MO may still be the effective HOMO. A reaction at the lone pair converts two nonbonding electrons into two bonding electrons, which is obviously highly favorable.
228. For experimental studies, see: Pacansky J., Chang J. S., Brown D. W., Schwarz W. J., J. Org. Chem., 1982, 47, 2233. Theoretical studies: Yamabe S., Minato T., Osamura Y., Chem. Commun., 1992, 26
229. Fang D., Fu X., Int. J. Quantum Chem., 1992, 44, 669
230. Sordo J. A., Gonzalez J., Sordo T. L., J. Am. Chem. Soc., 1992, 114, 6249
231. Cossio F. P., Ugalde J. M., Lopez X., Lecea B., Palomo C., J. Am. Chem. Soc., 1993, 115, 995
232. Lopez R., Sordo T. L., Sordo J. A., Gonzalez J., J. Org. Chem., 1993, 58, 7036
233. Assfeld X., Ruiz-Lopez M. F., Gonzalez J., Lopez R., Sordo J. A., Sordo T. L., J. Comput. Chem., 1994, 15, 479.
234. Remember that weakening a bond causes its HOMO to rise and its LUMO to fall (cf. p. 98). See also: Fukui K., Koga N., Fujimoto H., J. Am. Chem. Soc., 1981, 103, 196.
235. Minato T., Yamabe S., J. Am. Chem. Soc., 1988, 110, 4586.
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243. This unusual numbering is due to the Hückel software!
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249. Whereas optimization by STO-3G calculations leads to a planar structure for this model compound, both AM1 and PM3 calculations favor a gauche structure, the S=C-C=O dihedral angle being a 85°51' (AM1) and 91°76' (PM3).
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282. Lee P. S., Zhang X., Houk K. N., J. Am. Chem. Soc., 2003, 125, 5072.
283. In the in mode, the overlap between R and C4 is negative.
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285. Thomas B. E. IV, Evanseck J. D., Houk K. N., J. Am. Chem. Soc., 1993, 115, 4165. Geometry optimizations by 3-21 G calculations, energies calculated using Møller-Plesset theory and the 6-31G* basis set.
286. For this reason, in his vitamin B12 synthesis, Woodward initially predicted the wrong stereochemistry for the electrocyclization of a hexatriene. This led to the discovery of the conservation of orbital symmetry (Woodward R. B., in Aromaticity, Special Publication No. 21, Chemical Society, London, 1967, 217).
287. Evanseck J. D., Thomas B. E. IV, Houk K. N., J. Org. Chem., 1995, 60, 7134.
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495. Maximum frontier overlap thus encompasses the first two geometric constraints. We have detailed these, however, to show the preferential angles of attack.
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547. We saw a similar situation when dealing with 'ate' complexes (Exercise 3, p. 59).
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573. When the substituent is a conjugated group, this result can be immediately verified, using Coulson's equations (p. 18).
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581. We have implicitly assumed that cyclobutadiene is square. If it distorts and adopts a rectangular structure, its frontier orbitals become nondegenerate (Jahn-Teller effect) but the orbital separation will remain small and the molecule will still be highly reactive.
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588. Obviously, we can also rationalize these facts by saying that RO, Cl, RCO2, etc. are better leaving groups than H or R. However, it is always useful to look at a problem from different angles. For example, the present treatment can explain much more easily why the Meerwein-Ponndorf reaction is reversible (see below).
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614. We should not push this model too far however. Consider, for example, a 1-substituted hexadiene. In the limiting form B, the radical site at 1 is stabilized. Yet the transition state is late with the incipient 1-6 bond shorter than the partial 3-4 bond: apparently, the allyl radical 1-2-3 prefers to react by its less reactive site!
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620. Breslow R., Hoffmann J. M. Jr, J. Am. Chem. Soc., 1972, 94, 2111.
621. Coates et al. (ref. 66b) used a similar model.
622. Burrows C. J., Carpenter B. K., J. Am. Chem. Soc., 1981, 103, 6983.
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627. -1).
628. Yoo H. Y., Houk K. N., J. Am. Chem. Soc., 1997, 119, 2877
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630. In fact, MNDO and AM1 calculations predict an acceleration: Dewar M. J. S., Healy E. F, J. Am. Chem. Soc., 1984, 106, 7127
631. Dewar M. J. S., Jie C., J. Am. Chem. Soc., 1989, 111, 511.
632. Admittedly, the transition state is polarized and the 4-5-6 fragment bears a partial positive charge. However, as the substituent is put at position 5, which is a node for the allyl cation, the donor or attractor character of the substituent has little infl uence on the stability of the cation.
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650. Anh N. T., Maurel F., New J. Chem., 1997, 21, 861.
651. Ionic reactions in the gas phase are under charge control. See, e.g.: Faigle J. F. G., Isolani P. C., Riveros J. M., J. Am. Chem. Soc., 1976, 98, 2049
652. Comisarow M., Can. J. Chem., 1977, 55, 171
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663. Salem L., Electrons in Chemical Reactions, John Wiley & Sons, Inc., New York, 1982, Chapter 5.
664. Hoffmann R., Angew. Chem. Int. Ed. Engl., 1982, 21, 711.
665. Molecular mechanics can be used for many common compounds and is particularly effective in exploring conformer distribution.
666. Schaefer H. F. III, The Electronic Structure of Atoms and Molecules, Addison-Wesley, Reading, MA, 1972, p. 309.
667. See Section 8.3 for the definitions of various methods.
668. A potential surface is a graphical representation of the energy of the system as a function of its geometry. For a lucid account on potential energy surfaces, transition states, methods for calculating reaction paths, etc., see Chapter 2 in ref. 7.
669. Intrinsic reaction coordinate is a steepest-descent pathway which is required to pass through reactant, transition state and product.
670. Leforestier C., J. Chem. Phys., 1978, 68, 4406.
671. This average field is simply the field that would be provided if each of these electrons was a charge cloud and molecular orbitals allow us to calculate these clouds precisely.
672. More exactly, n is the number of basis functions. Therefore, a calculation using extended basis sets is more time consuming than the same calculation with a minimal basis set.
673. Caramella P., Houk K. N., Domelsmith L. N., J. Am. Chem. Soc., 1977, 99, 4511
674. Dewar M. J. S., J. Am. Chem. Soc., 1984, 106, 209
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676. Anh N. T., Frison G., Solladié-Cavallo A., Metzner P., Tetrahedron, 1998, 54, 12841.
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679. Anh N. T., Maurel F., Thanh B. T., Thao H. H., N'Guessan Y. T., New J. Chem., 1994, 18, 473
680. Anh N. T., Maurel F., Thao H. H., N'Guessan Y. T., New J. Chem., 1994, 18, 483.
681. These are the Hartree-Fock MOs and are kept fixed in the CI calculation.
682. CIS does not improve on the Hartree-Fock energy, as there is no interaction between the fundamental state and the singly excited states (Brillouin theorem). In CISD, the singly excited states can interact with the fundamental state through the intermediacy of the doubly excited states. We have met a similar situation in three orbital interactions (p. 27): two MOs belonging to the same molecule can interact if perturbed by a third MO belonging to another molecule.
683. The method is also called FORS (full optimized reaction space).
684. Tapia O., Goscinski O., Mol. Phys., 1975, 29, 1653
685. Miertus S., Scrocco E., Tomasi J., J. Chem. Phys., 1981, 55, 117
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689. The error comes from modeling cars by material points. If their lengths are taken into account, the speed cannot be reduced beyond a certain limit.
690. Delbecq F., Ilavsky D., Anh N. T., Lefour J. M., J. Am. Chem. Soc., 1985, 107, 1623.