Sulfur Dioxide Surrogates

The most significant driving force in the field of sulfur dioxide insertion has been the development of safe and bench-stable sulfur dioxide surrogates. To date, several sulfur dioxide surrogates have been developed and proved to be efficient in the proce

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Danqing Zheng Jie Wu

Sulfur Dioxide Insertion Reactions for Organic Synthesis 123

SpringerBriefs in Molecular Science

More information about this series at http://www.springer.com/series/8898

Danqing Zheng Jie Wu •

Sulfur Dioxide Insertion Reactions for Organic Synthesis

123

Danqing Zheng Department of Chemistry Fudan University Shanghai China

Jie Wu Department of Chemistry Fudan University Shanghai China

ISSN 2191-5407 ISSN 2191-5415 (electronic) SpringerBriefs in Molecular Science ISBN 978-981-10-4201-0 ISBN 978-981-10-4202-7 (eBook) DOI 10.1007/978-981-10-4202-7 Library of Congress Control Number: 2017935820 © The Author(s) 2017 This work is subject to copyright. All rights are reserved by the Publisher, whether the whole or part of the material is concerned, specifically the rights of translation, reprinting, reuse of illustrations, recitation, broadcasting, reproduction on microfilms or in any other physical way, and transmission or information storage and retrieval, electronic adaptation, computer software, or by similar or dissimilar methodology now known or hereafter developed. The use of general descriptive names, registered names, trademarks, service marks, etc. in this publication does not imply, even in the absence of a specific statement, that such names are exempt from the relevant protective laws and regulations and therefore free for general use. The publisher, the authors and the editors are safe to assume that the advice and information in this book are believed to be true and accurate at the date of publication. Neither the publisher nor the authors or the editors give a warranty, express or implied, with respect to the material contained herein or for any errors or omissions that may have been made. The publisher remains neutral with regard to jurisdictional claims in published maps and institutional affiliations. Printed on acid-free paper This Springer imprint is published by Springer Nature The registered company is Springer Nature Singapore Pte Ltd. The registered company address is: 152 Beach Road, #21-01/04 Gateway East, Singapore 189721, Singapore

Contents

1 Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

1 4

2 Sulfur Dioxide Surrogates . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

7 9

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11 12 12 17 24 26 26 33 44 46 46 58

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66 71 74

4 Conclusions and Outlook . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

79

3 Sulfur Dioxide Insertion Reactions. . . . . . . . . . . . . . . . . . . 3.1 Nucleophilic Addition with Organometallic Reagents . . 3.1.1 Synthesis of Sulfonamides . . . . . . . . . . . . . . . . 3.1.2 Synthesis of Sulfones . . . . . . . . . . . . . . . . . . . . 3.1.3 Synthesis of Sulfoxides . . . .