Reactions of butyllithium with sulfonylhydrazones

Kaufman, Gary M.; Cook, Francis Bernard; Shechter, Harold; Bayless, John H.; Friedman, Lester

doi:10.1021/ja00998a061

Cited by 59 publications

(17 citation statements)

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“…5,[4][5][6][7]7 (m,. -MS.: 338 ( 1 1, Mf), 220 (16), 209 (13), 205 (47), 123 (25), 105 (27), 95 (33), 93 (22), 91 (40), 83 (20), 81 (34), 79 (26), 77 (24), 69 (32), 67 (22), 57 (58), 55 (64), 53 (21), 43 (51), 41 (100).…”

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confidence: 99%

“…C(8)); 137,55 (s, C(9')); 144,94 (s, C(13')); 146,47 (s, C(13)); 147,26 (s, C(9)). -MS.: 550 (IS), 375 (7), 368 (6), 233 (13), 209 (14), 175 (25), 145 (22), 119 (43), 109 (23), 107 (34), 105 (55), 95 (45), 93 (32), 91 (41),83 (3% 81 (42), 79 (25), 77 (18), 69 (loo), 68 (27), 57 (34), 55 (61), 43 (48).…”

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confidence: 99%

“…-MS. : 538 272 (20), 271 (93), 270 (16), 268 (23), 251 (32), 233 (20), 214 (22), 213 (12), 199 (17), 189 (37), 187 (12), 186 (12), 175 (30), 173 (12), 171 (13), 161 (28), 159 (17), 149 (44), 148 (17), 147 (88), 135 (28), 133 (25), 131 (13), 129 (14), 128 (15), 123 (36), 122 (27), 119 (44), 117 (18), 115 (17), 109 (14), 107 (23), 106 (16), 105 (37), 95 (36), 94 (13), 93 (20), 91 (73), 81 (17), 79 (21), 77 (25) 43 (100).…”

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Synthese von Carotinoiden mit hydroxylierter Methylgruppe an der Polyenkette mit Hilfe von Vinyl‐Anionen (Shapiro‐Reaktion)

Bütikofer

Eugster

1983

Helvetica Chimica Acta

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Syntheses of Hydroxymethyl‐carotenoids Using Vinyl‐Anions Generated by the Shapiro‐Reaction A versatile synthesis of hydroxymethyl‐carotenoids with β‐ or ϵ‐end groups is presented. It makes use of the reactive vinyl anions prepared by the Shapiro‐reaction from (phenylsulfonyl)hydrazones of polyenones and their smooth 1,2‐addition to polyenals. Thus, e.g. (3R,6′R)‐β, ϵ‐carotene‐3, 19‐diol (72), an optically active model compound structurally very close to loroxanthin (1), has been synthesized.

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Synthese von Carotinoiden mit hydroxylierter Methylgruppe an der Polyenkette mit Hilfe von Vinyl‐Anionen (Shapiro‐Reaktion)

Bütikofer

Eugster

1983

Helvetica Chimica Acta

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“…Kaufinan and co-workers have reported (14) that lithium salts of tosylhydrazones decon~pose at a lower temperature t h a n the corresponding sodium salts. The metalloid compounds behave similarly, since treatment at room tempel.ature of the tosylhydrazones in tetrahydrofuran with nbutyllithium gives complete collversion to the corresponding diazoalkane.…”

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confidence: 99%

“…region rcgron the parent carbonyl compounds are known (14,18) to give tosylhydrazones which may be readily converted to the diazo compounds.…”

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The synthesis of silyl- and germyldiazoalkanes via tosylhydrazones

Brook¹,

Jones²

1969

Can. J. Chem.

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Tosylhydrazones have been prepared from acylsilanes and -germanes. These may be converted in excellent yield by 11-butyllithium to the metalloidal diazoalkanes tinder milder conditions than are required for the analogous carbon compounds. The diazoalkanes are far more stable than their carbon counterparts. These results, together with spectral shifts noted for the silyl and germyl compounds, are interpreted in terms of dn-pn bonding between the diazo group and the metalloid atom.

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Alkenes from Tosylhydrazones

Shapiro

2011

Organic Reactions

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In 1952, Bamford and Stevens observed that tosylhydrazones of aliphatic ketones yielded alkenes when treated with the sodium salt of ethylene glycol in boiling ethylene glycol. In addition to the alkene, molecular nitrogen, and p‐toluenesulfinate anion were produced. This chapter reviews such syntheses of alkenes from tosylhydrazones and the formation of cyclopropanes and acetylenes from tosylhydrazones because the several reactions involved are so closely interrelated. The four major reaction types are reviewed here: (1) base‐induced decomposition of tosylhydrazones in protic solvents and (2) in aprotic solvents (3) reactions of tosylhydrazones with alkyllithium reagents and (4) fragmentation reactions of alpha, beta‐epoxytosylhydrazones and analogous systems. Reactions 1 and 2 are called the protic and aprotic Bamford‐Stevens reaction.

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Reactions of butyllithium with sulfonylhydrazones

Cited by 59 publications

References 0 publications

Synthese von Carotinoiden mit hydroxylierter Methylgruppe an der Polyenkette mit Hilfe von Vinyl‐Anionen (Shapiro‐Reaktion)

Synthese von Carotinoiden mit hydroxylierter Methylgruppe an der Polyenkette mit Hilfe von Vinyl‐Anionen (Shapiro‐Reaktion)

The synthesis of silyl- and germyldiazoalkanes via tosylhydrazones

Alkenes from Tosylhydrazones

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