N-alkylation of sulfilimines and sulfoximines

Sulfoximines: Structures, Properties and Synthetic Applications

“…Some years later purely aliphatic Type I sulfoximines have been synthesised using the same route. 23,135,136 When both C-atoms in a Type I sulfoximine (Scheme 29) were members of aromatic ring systems the hydrazoic acid imination procedure failed and alternative routes had to be used. This was exemplified in 1974 by Stoss and Satzinger, both of them industrial chemists at the Gödecke AG (Scheme 34).…”

The structure of dehydromethionine. An azasulfonium salt

“…The packing of the molecules in the unit cell is illustrated in Figure 3. Final atomic positional and thermal parameters are given in Tables II and Journal of the American Chemical Society j 98:4 j February ¡8,1976 8) 0.70807 (5) 0.02654 ( 27) 0.01171 (12) 0.00307 (4) -0.00066 ( 12) 0.00256 ( 7) 0.00036 ( 5) N 1.1017 (4) 0.6786 (3) 0.60757 ( 16) 0.0250 (8) 0.0109 (4) 0.00321 (13) 0.0006 (5) 0.00218 (24) -0.00058 ( 19) 0(1) 1.1006 (5) 0.85089 ( 27) 0.36984( 16) 0.0754 (15) 0.0146 (4) 0.00381 (12) -0.0004 ( 5) 0.0071 (3) 0.00145 ( 17) 0(2) 1.1242 (4) 0.61024 (23) 0.41348 (15) 0.0535 (11) 0.0120 (3) 0.00480 ( 14) -0.0041 (4) 0.0084 (3) -0.00163 ( 15) C(l) 0.6784 (5) 0.7758 (5) 0.64797 ( 22) 0.0189 (9) 0.0193 (6) 0.00418 (17) 0.0003 (6) 0.0007 (3) -0.00091 (26) C(2) 0.7377 (6) 0.7886 (5) 0.54032 ( 22) 0.0247 (10) 0.0183 (5) 0.00385 ( 16) 0.0031 (6) 0.0010 (3) 0.00022 ( 25) C(3) 1.0098 ( 5) 0.7885 (3) 0.53377 (18) 0.0245 (9) 0.0098 (4) 0.00309 ( 14) -0.0013 (5) 0.00152 (28) -0.00031 (18) C( 4) 1.0875 ( 5) 0.7455 (3) 0.42994 (18) 0.0278 (10) 0.0125 (4) 0.00323 (15) -0.0034 (5) 0.00254 (29) -0.00064 ( 21) C( 5) 1.0710 (6) 0.8484 (4) 0.77051 (23) 0.0287 (11) 0.0160 (5) 0.00332( 16) -0.0014 ( 6) 0.0007 (3) -0.00155 (24) Table III 1.9( 5) H( 6) 1.081 ( 5) 0.606 (3) 0.5859 (20) 2.2 ( 7) H( 7) 0.968 (5) 0.868 (3) 0.8220 (…”

“…5 The formation of azasulfonium salts by the reaction of sulfilimines with electrophiles has also been studied. 6,7 The determination of the structures of azasulfonium salts is of interest to facilitate an understanding of their reactions and to reveal the nature of the bonding of the sulfur atom. This latter concern involves two major considerations: (1) the sulfur atom may be trivalent or tetravalent and (2) there may be p(N)-d(S) bonding.…”

A Metal‐free Access to HinderedN‐Alkyl Sulfoximines via In‐Situ Generated Aza‐Oxyallyl Cations from Functionalized Alkyl Bromide

“…[14] Despite these advances of N-alkyl sulfoximines in natural product and drug discovery, [9] limited progress has been made towards the N-alkylation of sulfoximines due to their low nucleophilicity. [15] Consequently, substantial efforts have been devoted to the synthesis of N-alkyl sulfoximines by various routes, including base catalyzed Michael-type additions, [16] Eschweiler-Clark type methylations [17] nucleophilic substitutions, [18] and two step acylation/reduction sequences [19] (Scheme 1, equation 1).…”