Radical ring‐opening polymerization of five‐membered cyclic vinyl sulfone using p‐toluenesulfonyl halides

Abstract

Radical ring-opening polymerizations of a five-membered cyclic vinyl sulfone monomer, 2-vinylthiolane-1,1-dioxide (VTDO), was carried out by using p-toluenesulfonyl iodide (TosI) and bromide (TosBr) as radical initiators, and the corresponding ring-opened polymer (PVTDO) was obtained. Both TosI and TosBr were found to work as the radical initiators for the polymerization of VTDO in bulk. The use of TosI gave PVTDOs with a broad, multimodal distribution of molecular weight in low yields. When 10 mol % of TosBr was employed, the isolated yield of PVTDO reached 49%, and the obtained PVTDO had a relatively narrow, monomodal molecular weight distribution of 1.8 with an M n of 4100.

Radical Ring-Opening Polymerization: Scope, Limitations, and Application to (Bio)Degradable Materials

“…The polymerization mechanism was clearly based on a ring-opening process. 75,76 Conversely, CVS2 was more difficult to polymerize since only 60% conversion were reached after 12 h at 80 °C in the presence of BPO and with only 40% of ring-opening. CVS3 was situated in between CVS1 and CVS2 as it partially polymerized by ring-opening like CVS2 (85%) but reached high conversion, similar to CVS1.…”

Synthesis and characterization of novel poly(sulfone siloxane)s with good solubility and recyclability based on siloxane units

“…Aliphatic polysulfones are favored for high glass transition temperature ( T g ), which demands a high processing temperature. 33,39,40 In contrast, the T g of the presented poly(sulfone siloxane)s were considerably low with values from −14 °C to 11 °C, as shown in Fig. 5.…”

Imino‐λ3‐iodane and Catalytic Amount of I2‐Mediated Synthesis ofN‐Allylsulfenamides via [2,3]‐Sigmatropic Rearrangement

“…X‐ray crystal analysis was performed by Rigaku RAPID II XRD Image Plate using graphite‐monochromated Cu‐ K α radiation ( λ = 1.54187 Å) at 173 K. Please see the supporting information or the cif file for more detailed crystallography information. Cyclohex‐2‐en‐1‐yl(phenyl)sulfane 1e , [ 15 ] (3‐methylbut‐2‐en‐1‐yl)(phenyl)sulfane 1g , [ 16 ] and 2‐vinyltetrahydrothiophene 1h [ 17 ] were prepared according to the reported procedures. Various imino‐λ 3 ‐iodanes 2 ( 2a , [ 18 ] 2b, c , [ 19 ] 2d [ 14h ] ) were prepared according to the reported procedures.…”