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• W2756105622 endingPage "14247" @default.
• W2756105622 startingPage "14231" @default.
• W2756105622 abstract "Abstract t BuCH=C(Li)S(O)( NSO 2 Tol )Ph ⋅ L (L=2THF, TMEDA) ( 1⋅ L) in THF solution is a monomer with a C−Li bond according to NMR spectroscopy and cryoscopy. It was identified as CIP through the scalar 13 C, 6 Li coupling and 6 Li,{ 1 H} NOE experiments. The CIP has a six‐membered C‐Li‐O‐S‐N‐S chelate ring structure. 6 Li, 1 H FUCOUP and 6 Li, 1 H HMQC NMR experiments of 1⋅ TMEDA revealed a scalar 6 Li, 1 H coupling across the Li−C=C−H bonds. According to the NMR data the π‐bond of 1⋅ L is polarized by the negative charge of the anionic C atom. t BuCH=C(Li)S(O)( NMe )Ph ( 2⋅ L) is most likely also a monomer with a C−Li bond. According to 6 Li,{ 1 H} NOE experiments it has a four‐membered C‐Li‐N‐S chelate ring structure. 13 C NMR spectroscopy showed the C−Li bonds of 1⋅ L and 2⋅ L to be fluxional. 1 H NMR spectroscopy and 1D TOCSY experiments of Ph 2 C=C(Li)S(O)( NSO 2 Tol )Ph revealed topomerization of the phenyl groups, which is attributed to a fast positional exchange of the Li atom and the sulfonimidoyl group. The fluxionality of the C−Li bond and the interchange of the Li atom and the sulfonimidoyl group at the anionic C atom of sulfonimidoyl vinyllithiums, which result in a low configurational stability, most likely involve the formation of O , Li and N , Li CIPs through heterolysis of the C−Li bond. Ab initio calculation of MeCH=C(Li)S(O)( NMe )Ph yielded an energy minimum structure with a C−Li bond, a four‐membered C‐Li‐N‐S chelate ring and a strongly expanded C=C−Li bond angle. According to calculation of MeCH=C(Li)S(O)( NMe )Ph, [MeCH=CS(O)( NMe )Ph] − and MeCH=C(H)S(O)( NMe )Ph deprotonation is not accompanied by a shortening of the C−S bond. Ab initio calculation of MeCH=C(Li)S(O)( NSO 2 Me )Ph gave a structure with a C−Li bond and a six‐membered C‐Li‐O‐S‐N‐S chelate ring. 6 Li, 1 H NOE experiments and cryoscopy of LiCH 2 S(O)( NSO 2 Tol )Ph ( 3 ) revealed a monomeric CIP with a C−Li bond. The CIP has a six‐membered C‐Li‐O‐S‐N‐S chelate ring structure found in polymeric 3 in the crystal." @default.
• W2756105622 created "2017-09-25" @default.
• W2756105622 creator A5002312686 @default.
• W2756105622 creator A5052953262 @default.
• W2756105622 creator A5075289770 @default.
• W2756105622 creator A5080612612 @default.
• W2756105622 date "2017-09-12" @default.
• W2756105622 modified "2023-09-27" @default.
• W2756105622 title "Experimental and Computational Studies of the Structure of Sulfonimidoyl Vinyllithiums" @default.
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