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In their analysis of experiments and in their planning of
syntheses, organic
chemistsconsciouslyorunconsciouslytendtousetheprincipleofleastmotion,
thechemicalequivalentofOccam'srazor.
Inrearrangementreactionsthispr- ciple is violated and may make
rearrangements problematic reactions. At the sametime,
thereisalwaysfascinationintheunexpectedandsorearrangement
reactionsarealsoanattractive?eldofstudy. Consequently,
ourunderstanding of rearrangement reactions is now quite advanced
and allows strategic uses in organic synthesis. Here, a helpful
tool that may easily be overlooked is thein?uence
oforganosulfurfunctionalitiesontheserearrangements. Infact, the
presence of sulfur may make rearrangements predictable and
productive or allow speci?c transformations which would otherwise
require a tedious synthetic detour. The present account is meant to
spread this knowledge. In addition, an introductory chapter gives a
survey of the basics of organosulfur chemistry to put the
information in the individual chapters into perspective and to help
readers who are less familiar with the peculiarities of sulfur in
an organicenvironment.
Theamountofmaterialrequiringcoveragewassovastthatthevolumehadto
besplitintotwoparts.
Wehopethatreaderswillappreciatethecomprehensive and up-to-date
information on sulfur-mediated rearrangements. Fortunately, leading
experts were available to write the individual chapters and provide
state-of-the-artreviews ofthecurrent researchonsulfur-mediated
rearran- ments. It was a pleasure to work with these colleagues and
I appreciate their involvement in spite of many other obligations.
This volume should help the chemical community in their synthetic
workand so it was worththe effort. Clausthal-Zellerfeld, October
2006 Ernst Schaumann Contents
SulfurisMoreThantheFatBrotherofOxygen.
AnOverviewofOrganosulfurChemistry E. Schaumann. . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . 1
RecentAdvancesinPummererReactions S. Akai.Y. Kita . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . 35 1,2-SulfurMigrations
A. W. Sromek.V. Gevorgyan. . . . . . . . . . . . . . . . . . . . .
. . . 77 1,3-SulfurShifts: MechanismandSyntheticUtility S. K. Bur.
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
125 AuthorIndexVolumes251-274. . . . . . . . . . . . . . . . . . .
. . . 173 Subject Index. . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . 183 ContentsofVolume275
Sulfur-MediatedRearrangementsII Volume Editor: Ernst Schaumann
ISBN: 978-3-540-68099-4 2,3]-Sigmatropic RearrangementsofAllylic
Sulfur Compounds M. Reggelin 2,3]Sigmatropic
RearrangementsofPropargylic andAllenicSystems S. Braverman .M."
In their analysis of experiments and in their planning of
syntheses, organic
chemistsconsciouslyorunconsciouslytendtousetheprincipleofleastmotion,
thechemicalequivalentofOccam'srazor.
Inrearrangementreactionsthispr- ciple is violated and may make
rearrangements problematic reactions. At the sametime,
thereisalwaysfascinationintheunexpectedandsorearrangement
reactionsarealsoanattractive?eldofstudy. Consequently,
ourunderstanding of rearrangement reactions is now quite advanced
and allows strategic uses in organic synthesis. Here, a helpful
tool that may easily be overlooked is thein?uence
oforganosulfurfunctionalitiesontheserearrangements. Infact, the
presence of sulfur may make rearrangements predictable and
productive or allow speci?c transformations which would otherwise
require a tedious synthetic detour. The present account is meant to
spread this knowledge. In addition, an introductory chapter gives a
survey of the basics of organosulfur chemistry to put the
information in the individual chapters into perspective and to help
readers who are less familiar with the peculiarities of sulfur in
an organicenvironment.
Theamountofmaterialrequiringcoveragewassovastthatthevolumehadto
besplitintotwoparts.
Wehopethatreaderswillappreciatethecomprehensive and up-to-date
information on sulfur-mediated rearrangements. Fortunately, leading
experts were available to write the individual chapters and provide
state-of-the-artreviews ofthecurrent researchonsulfur-mediated
rearran- ments. It was a pleasure to work with these colleagues and
I appreciate their involvement in spite of many other obligations.
This volume should help the chemical community in their synthetic
workand so it was worththe effort. Clausthal-Zellerfeld, October
2006 Ernst Schaumann Contents
SulfurisMoreThantheFatBrotherofOxygen.
AnOverviewofOrganosulfurChemistry E. Schaumann. . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . 1
RecentAdvancesinPummererReactions S. Akai.Y. Kita . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . 35 1,2-SulfurMigrations
A. W. Sromek.V. Gevorgyan. . . . . . . . . . . . . . . . . . . . .
. . . 77 1,3-SulfurShifts: MechanismandSyntheticUtility S. K. Bur.
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
125 AuthorIndexVolumes251-274. . . . . . . . . . . . . . . . . . .
. . . 173 Subject Index. . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . 183 ContentsofVolume275
Sulfur-MediatedRearrangementsII Volume Editor: Ernst Schaumann
ISBN: 978-3-540-68099-4 2,3]-Sigmatropic RearrangementsofAllylic
Sulfur Compounds M. Reggelin 2,3]Sigmatropic
RearrangementsofPropargylic andAllenicSystems S. Braverman .M."
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