Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Journal of the American Chemical Society called Aromatic silicon systems. II. The silacyclopentadienide anion, Author is Benkeser, Robert A.; Grossman, Richard F.; Stanton, Garth M., which mentions a compound: 97739-46-3, SMILESS is CC1(C2)OC(C3)(C)OC2(C)OC3(C)P1C4=CC=CC=C4, Molecular C16H21O3P, Recommanded Product: 97739-46-3.
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