7251-15-2

Usage

Molecular Structure

A phosphorus-containing heterocycle with multiple prop-2-en-1-yloxy (allyloxy) groups attached to a triazatriphosphinine core.

Classification

Member of the phosphinine family, which is a group of phosphorus-containing heterocycles.

Reactivity

High reactivity due to the presence of the allyloxy groups.

Potential Applications

a. Ligand in metal coordination chemistry.
b. Reagent for organic synthesis.
c. Material science for the preparation of advanced polymers or functional materials.

Unique Features

The compound's unique structure and reactivity make it an interesting target for further study and potential industrial applications.

Upstream product

• 107-18-6 allyl alcohol 

Relevant academic research and scientific papers

Ring-closing metathesis reactions of terminal alkene-derived cyclic phosphazenes

The first examples of ring-closing metathesis (RCM) reactions of a series of terminal alkene-derived cyclic phosphazenes have been carried out. The tetrakis-, hexakis-, and octakis(allyloxy)cyclophosphazenes (NPPh 2)(NP(OCH2CH = CH2)2)2 (1), N3P3(OCH2CH = CH2)6 (2), and N4P4(OCH2CH = CH2) 8 (3) and the tetrakis(allyloxy)-S-phenylthionylphosphazene (NS(O)Ph)[NP(OCH2CH = CH2)2]2 (4) were prepared by the reactions of CH2 = CHCH2ONa with the cyclophosphazenes (NPPh2)(NPCl2)2, N 3P3Cl6, and N4P4Cl 8 and the S-phenylthionylphosphazene (NS(O)Ph)(NPCl2) 2. The reactions of 1-4 with Grubbs first-generation olefin metathesis catalyst Cl2Ru = CHPh(PCy3)2 resulted in the selective formation of seven-membered di-, tri-, and tetraspirocyclic phosphazene compounds (NPPh2)[NP(OCH2CH = CHCH2O)]2 (5), N3P3(OCH 2CH = CHCH2O)3 (6), and N4P 4(OCH2CH = CHCH2O)4 (7) and the dispirocyclic S-phenylthionylphosphazene compound (NS(O)Ph)[NP(OCH2CH = CHCH2O)]2 (8). X-ray structural studies of 5-8 indicated that the double bond of the spiro-substituted cycloalkene units is in the cis orientation in these compounds. In contrast to the reactions of 1-4, RCM reactions of the homoallyloxy-derived cyclophosphazene and thionylphosphazene (NPPh2)[NP(OCH2CH2CH = CH2) 2]2 (9) and (NS(O)Ph)[NP(OCH2CH2CH = CH2)2]2 (10) with the same catalyst resulted in the formation of 11-membered diansa compounds NPPh2[NP(OCH 2CH2CH = CHCH2CH2O)]2 (11) and (NS(O)Ph)[NP(OCH2CH2CH = CHCH2CH 2O)]2 (13) and the intermolecular doubly bridged ansa-dibino-ansa compounds 12 and 14. The X-ray structural studies of compounds 11 and 13 indicated that the double bonds of the ansa-substituted cycloalkene units are in the trans orientation in these compounds. The geminal bis(homoallyloxy)tetraphenylcyclotriphosphazene [NPPh2] 2[NP(OCH2CH2CH = CH2)2] (15) upon RCM with Grubbs first- and second-generation catalysts gave the spirocyclic product [NPPh2]2[NP(OCH2CH 2CH = CHCH2CH2O)] (16) along with the geminal dibino-substituted dimeric compound [NPPh2]2[NP(OCH 2CH2CH = CHCH2CH2O) 2PN][NPPh2]2 (17) as the major product. The dibino compound 17, upon reaction with the Grubbs second-generation catalyst, was found to undergo a unique ring-opening metathesis reaction, opening up the bino bridges and partially converting to the spirocyclic compound 16.