1202583-22-9

Basic information

• Product Name: [2,2,6,6-tetramethylpiperidinium][C₄H₃SCCB(pentafluorophenyl)3]
• Synonyms: [2,2,6,6-tetramethylpiperidinium][C₄H₃SCCB(pentafluorophenyl)3]
• CAS NO: 1202583-22-9
• Molecular Weight: 761.405
• Mol File: 1202583-22-9.mol

Chemical Properties

• CAS DataBase Reference: [2,2,6,6-tetramethylpiperidinium][C₄H₃SCCB(pentafluorophenyl)3](CAS DataBase Reference)
• NIST Chemistry Reference: [2,2,6,6-tetramethylpiperidinium][C₄H₃SCCB(pentafluorophenyl)3](1202583-22-9)
• EPA Substance Registry System: [2,2,6,6-tetramethylpiperidinium][C₄H₃SCCB(pentafluorophenyl)3](1202583-22-9)

Safety Data

• Hazardous Substances Data: 1202583-22-9(Hazardous Substances Data)

Upstream product

• 768-66-1 2,2,6,6-tetramethyl-piperidine 
• 67237-53-0 3-ethynylthiophene 
• 1109-15-5 tris(pentafluorophenyl)borate 

Relevant articles and documents

Activation of terminal alkynes by frustrated lewis pairs

The reactions of frustrated Lewis pairs (FLPs) derived from B(C 6F5)3 and the bulky Lewis bases 2,2,6,6-tetramethylpiperidine (TMP), tri-tert-butylphosphine, and lutidine (Lut) with terminal alkynes (acetylene, phenylacetylene, 3-ethynylthiophene) were investigated. The FLPs TMP ... B(C6F5)3, t-Bu3P ...B(C6F5)3 and Lut ... (C6F5)3 reacted with acetylene (HC=CH) to yield the apparently thermodynamically more stable Eisomers [TMPH][(C 6F5)2B-C(C6F5)=C(H) B(C6F5)3] (1-E), t-Bu3PC(H)-C(H) B(C6F5)3 (2-E; 90%), and [t-Bu 3PH][C6F5)2B-C(C6F 5)=C(H)B(C6F5)3] (3-E; 10%), and LutC(H)=C(H)B(C6F5)3 (4-E), respectively. A mechanistic pathway for the reaction of acetylene is suggested to start with the formation of a weak B(C6F5)3/acetylene adduct followed by a deprotonation of this species with any mentioned Lewis bases (LB), yielding the acetylide salts [LBH][(C6F5)3BC=CH]. Alternatively, nucleophilic addition of the LB to this adduct occurs to yield LBC(H)=C(H)B(C6F5)3 compounds. Formation of 1 and 3-E is explained by the reactions of [LBH][B(C6F 5)3C=CH] salts with a second equivalent of B(C 6F5)3 to undergo electrophilic addition, forming the vinylidene adduct (C6F5)3B -C+=C(H)B(C6F5)3, which is subsequently stabilized by 1,2-migration of a C6F5 group to form [(C6F5)2BC(C6F 5)=C(H)B(C6F5)3]. The reaction between B(C6F5)3 and phenylacetylene yielded a mixture of (Z)- and (E)-PhC(H)=C(C6F5)B(C 6F5)2 (H-Z and 11-E), confirming that the reaction proceeds via an acetylene/vinylidene rearrangement and subsequent 1,2-shift of a C6F5 group to the carbenic center. The FLPs TMP ...B(C6F5)3 and tBu 3P... B(C6F5)3 were converted with phenylacetylene or 3-ethynylthiophene to yield the acetylide products [TMPH][PhC=CB(C6F5)3] (5), [TMPH][SC 4H3C=CB(C6F5)3] (6), [t-Bu 3PH][PhC≡ CB(C6F5)3] (7), and [t-Bu3PH][SC4H3C≡CB(C6F 5)3] (8), where TMP and t-Bu3P acted as a base deprotonating the acetylenic proton. When the FLP Lut ... B(C 6F5)3 was reacted with phenylacetylene or 3-ethynylthiophene, the deprotonated product [LutH][PhC=CB(C6F 5)3] (9; 47%) and the 1,2-addition compound LutC(SC 4H3C)=C(H)B(C6F5)3 (10; 55%) were obtained. Compounds 1-E, 2-E, 5, and 6 were characterized by X-ray diffraction studies.