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1,2-Sulfur Migrations

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Sulfur-Mediated Rearrangements I

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 274))

Abstract

1,2-Thio migration has emerged as a valuable synthetic tool for organic chemists. The most common route of 1,2-thio migration proceeds through a thiiranium intermediate. The latter usually proceeds stereoselectively, since substitution of a vicinal leaving group of sulfur takes place with good stereocontrol; substitution or elimination to open the thiiranium ring also proceeds stereoselectively. This and other types of 1,2-thio migration, including 1,2-thio shifts, formal 1,2-thio migration through fragmentation-recombination, [1,5]∼thio migration in five-membered ring systems, and radical 1,2-thio migrations are discussed in this review.

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Abbreviations

1o :

primary

2o :

secondary

4A MS:

four Angstrom molecular sieves

Ac:

acetyl

AIBN:

2,2′-azobisisobutyronitrile

Ar:

aryl

Bn:

benzyl

Bz:

benzoyl

CDI:

carbonyl diimidazole

DAST:

diethylamino sulfur trifluoride

DEAD:

diethyl azodicarboxylate

DMAP:

N,N-dimethylaminopyridine

DMA:

N,N-dimethylacetamide

DMF:

N,N-dimethylformamide

DMS:

dimethylsulfide

DMSO:

dimethylsulfoxide

d.r.:

diastereomeric ratio

E:

electrophile

ee:

enantiomeric excess

Et:

ethyl

hv :

irradiation; light

IBX:

2-iodoxybenzoic acid

LA:

Lewis acid

LG:

leaving group

m-CPBA:

meta-chloroperoxybenzoic acid

Me:

methyl

MOM:

methoxymethyl

Ms:

mesyl

naphth:

naphthyl

Nu:

nucleophile

NBS:

N-bromosuccinimide

NCS:

N-chlorosuccinimide

NIS:

N-iodosuccinimide

n-Pr:

normal-propyl

p :

para

Ph:

phenyl

Phth:

phthalimido

PMB:

para-methoxybenzyl

PMP:

para-methoxyphenyl

PNB:

para-nitrobenzyl

PPh3 :

triphenylphosphine

Pv:

pivaloyl

rt:

room temperature

TBS:

tert-butyldimethylsilyl

t-Bu:

tert-butyl

TEAB:

tetraethylammonium bromide

TES:

triethylsilyl

TIPS:

triiso-propylsilyl

Tf:

trifluoromethanesulfonyl

TFAA:

trifluoroacetic acid

Tr:

trityl; triphenylmethyl

Ts:

para-toluenesulfonyl

TsOH:

para-toluenesulfonic acid

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Acknowledgments

The support of the National Institutes of Health (GM-6444) is gratefully acknowledged.

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Authors and Affiliations

  1. University of Illinois at Chicago, Department of Chemistry, 845 W. Taylor St. Rm. 4500 SES (m/c 111), 60607, Chicago, Illinois, USA

    Anna W. Sromek & Vladimir Gevorgyan

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  1. Anna W. Sromek
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  2. Vladimir Gevorgyan
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Correspondence to Vladimir Gevorgyan .

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Ernst Schaumann

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Sromek, A.W., Gevorgyan, V. (2006). 1,2-Sulfur Migrations. In: Schaumann, E. (eds) Sulfur-Mediated Rearrangements I. Topics in Current Chemistry, vol 274. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_057

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