The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Aromatic silicon systems. II. The silacyclopentadienide anion》. Authors are Benkeser, Robert A.; Grossman, Richard F.; Stanton, Garth M..The article about the compound:1,3,5,7-Tetramethyl-6-phenyl-2,4,8-trioxa-6-phosphaadamantanecas:97739-46-3,SMILESS:CC1(C2)OC(C3)(C)OC2(C)OC3(C)P1C4=CC=CC=C4).Application of 97739-46-3. Through the article, more information about this compound (cas:97739-46-3) is conveyed.
cf. ibid. 4723. Silacyclopentadiene (I) has been found to react directly with K forming H and II. Comparison of the nuclear magnetic resonance spectra of I and II provides graphic evidence that it is the silanic hydrogens which are replaced by the metal in this reaction. Significantly, divinylsilane (the open chain analog of I) does not react with K at any appreciable rate under comparable conditions. This suggests that resonance stabilization of the silacyclopentadienide anion is providing a driving force for this reaction. II reacts with bromobenzene forming a mixture of 1-phenyl- and 1,1-diphenylsilacydopentadiene. The structure of the latter two compounds was established by reducing them catalytically to phenylated silacydopentanes which, in turn, could be prepared by unequivocal routes. II is colored in tetrahydrofuran solutions and possesses a spectrum which is quite similar to K in the visible region. All of the foregoing observations point to some measure of resonance stabilization in the silacyclopentadienide ring system, suggesting that the “”Hueckel rule”” will enjoy some success in predicting aromatic character for certain silicon ring systems
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Reference:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics