Synthesis of laddersiloxanes by novel stereocontrolled approach

Three new pentacyclic laddersiloxanes were prepared by a new method utilizing single stereoisomer of disiloxanediol as a growing unit. Thus, one diastereomer of disiloxanediol, (RS)–[i-PrPhSi(OH)]2O was isolated and treated with tetrachlorocyclotetrasiloxane, resulting in the formation of tricyclic laddersiloxanes with cis-Ph groups at terminals. All of the obtained isomers could be transformed into pentacyclic laddersiloxanes by dephenylchlorination followed by the reaction with (RS)–[i-PrPhSi(OH)]2O. The structures of new tricyclic and pentacyclic laddersiloxanes were determined by X-ray crystallography. The thermogravity properties of laddersiloxanes depending on the molecular weight and structures were summarized.

Graphical abstractThree new pentacyclic laddersiloxanes were prepared by a new method utilizing single stereoisomer of disiloxanediol as a growing unit. Thus, (RS)–[i-PrPhSi(OH)]2O was isolated and treated with tetrachlorocyclotetrasiloxane, resulting in the formation of tricyclic laddersiloxanes with cis-Ph groups at terminals. All of the obtained isomers could be transformed into pentacyclic laddersiloxanes.Figure optionsDownload full-size imageDownload as PowerPoint slide