{"product_id":"cyclopropanes-in-organic-synthesis-isbn-9781118057438","title":"Cyclopropanes in Organic Synthesis","description":"This is a practical guidebook about cyclopropanes that thoroughly surveys derivatives and transformations, synthetic methods, and experimental efficiency as a gateway for further research and development in the field.\u003cbr\u003e\u003cbr\u003e•    Provides comprehensive lists and synthetically-oriented synopses of cyclopropane chemistry review references along with publication data on applications in the syntheses of natural and related biologically active compounds\u003cbr\u003e•    Acts as a resource to help readers better understand cyclopropane applications for the efficient realization of synthetically important organic transformations and popular experimental procedures\u003cbr\u003e•    Includes new developments and up-to-date information that will lead to original methodologies for complex organic synthesis\u003cbr\u003e•    Stresses universality, flexibility, and experimental efficiency of a strategy based on preparing cyclopropane derivatives and performing ring cleavage reactions with inexpensive reagents\u003cbr\u003e•    Focuses on the synthetic potential of cyclopropane applications, for example  the synthesis of natural compounds and other target-oriented syntheses via cyclopropane intermediaries, as well on their planning by retrosynthetic analysis \u003cp\u003ePreface ix\u003c\/p\u003e \u003cp\u003e\u003cb\u003ePart I Reactivity and availability 1\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003eIntroduction, 1\u003c\/p\u003e \u003cp\u003eReference, 2\u003c\/p\u003e \u003cp\u003e\u003cb\u003e1 Structure and Reactivity of the Cyclopropane Species 3\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e1.1 Geometry and Bonding, 3\u003c\/p\u003e \u003cp\u003e1.2 Energy, 4\u003c\/p\u003e \u003cp\u003e1.3 Spectra, 5\u003c\/p\u003e \u003cp\u003e1.4 Cyclopropyl Cations, 5\u003c\/p\u003e \u003cp\u003e1.5 Cyclopropyl Anions, 6\u003c\/p\u003e \u003cp\u003e1.6 Cyclopropyl Radicals, 7\u003c\/p\u003e \u003cp\u003e1.7 Cyclopropylidenes, 7\u003c\/p\u003e \u003cp\u003e1.8 Cyclopropylcarbinyl Cations, 8\u003c\/p\u003e \u003cp\u003e1.9 Cyclopropylcarbinyl Anions, 8\u003c\/p\u003e \u003cp\u003e1.10 Cyclopropylcarbinyl Radicals, 10\u003c\/p\u003e \u003cp\u003e1.11 Cyclopropylcarbenes, 10\u003c\/p\u003e \u003cp\u003e1.12 Conclusion, 11\u003c\/p\u003e \u003cp\u003eReferences, 13\u003c\/p\u003e \u003cp\u003e\u003cb\u003e2 Ring Cleavage Reactions 15\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e2.1 Cyclopropyl Activation, 16\u003c\/p\u003e \u003cp\u003e2.1.1 Halogen, Oxy, and Sulfur Substituted Cyclopropanes, 16\u003c\/p\u003e \u003cp\u003e2.1.2 Alkylidenecyclopropanes, 19\u003c\/p\u003e \u003cp\u003e2.2 Cyclopropylcarbinyl Activation, 23\u003c\/p\u003e \u003cp\u003e2.2.1 Halogeno, Oxy, Acyl and Metallomethyl Cyclopropanes, 23\u003c\/p\u003e \u003cp\u003e2.2.2 Alkylidenecyclopropanes, 27\u003c\/p\u003e \u003cp\u003e2.2.3 Vinyl and Ethynyl Cyclopropanes, 29\u003c\/p\u003e \u003cp\u003e2.2.4 1,2]Divinylcyclopropanes, 33\u003c\/p\u003e \u003cp\u003e2.2.5 Acceptor Cyclopropanes, 35\u003c\/p\u003e \u003cp\u003e2.2.6 Donor Cyclopropanes, 38\u003c\/p\u003e \u003cp\u003e2.2.7 Donor–Acceptor Cyclopropanes, 43\u003c\/p\u003e \u003cp\u003e2.3 Conclusion, 48\u003c\/p\u003e \u003cp\u003eReferences, 49\u003c\/p\u003e \u003cp\u003e\u003cb\u003e3 Synthesis of Cyclopropanes 57\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e3.1 1,3]Cyclization Reactions, 57\u003c\/p\u003e \u003cp\u003e3.1.1 Cyclizations with Cleavage of Two Single Bonds, 58\u003c\/p\u003e \u003cp\u003e3.1.2 Cyclizations with Cleavage of One Double Bond and One Single Bond, 59\u003c\/p\u003e \u003cp\u003e3.1.3 Cyclizations with Cleavage of Two Double Bonds, 62\u003c\/p\u003e \u003cp\u003e3.2 [2 + 1] Cyclization Reactions, 65\u003c\/p\u003e \u003cp\u003e3.2.1 Cycloaddition of Carbene Equivalents to Olefins, 66\u003c\/p\u003e \u003cp\u003e3.2.2 Coupling of 1,1]Carbodianion and 1,2]Carbodication Equivalents, 79\u003c\/p\u003e \u003cp\u003e3.2.3 Coupling of 1,1]Carbodication and 1,2]Carbodianion Equivalents, 83\u003c\/p\u003e \u003cp\u003e3.3 Addition Reactions to the Double Bond of Cyclopropenes, 88\u003c\/p\u003e \u003cp\u003e3.4 Interconversion of Cyclopropanes, 90\u003c\/p\u003e \u003cp\u003e3.5 Conclusion, 90\u003c\/p\u003e \u003cp\u003eReferences, 90\u003c\/p\u003e \u003cp\u003e\u003cb\u003ePart Ii Synthetic Application 99\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003eIntroduction, 99\u003c\/p\u003e \u003cp\u003eReferences, 100\u003c\/p\u003e \u003cp\u003e\u003cb\u003e4 Triangulation Retrosynthetic Analysis 103\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e4.1 Retrosynthetic Triangulation, 103\u003c\/p\u003e \u003cp\u003e4.2 Conclusion, 108\u003c\/p\u003e \u003cp\u003eReferences, 108\u003c\/p\u003e \u003cp\u003e\u003cb\u003e5 Acyclic Compounds 109\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e5.1 Formation of Carbon Substituents, 109\u003c\/p\u003e \u003cp\u003e5.1.1 Nonactivated Cyclopropane Precursors, 109\u003c\/p\u003e \u003cp\u003e5.1.2 Cyclopropylcarbinyl Activated Precursors, 112\u003c\/p\u003e \u003cp\u003e5.1.3 Cooperatively Activated Precursors, 138\u003c\/p\u003e \u003cp\u003e5.2 Formation of Olefin Groups, 139\u003c\/p\u003e \u003cp\u003e5.2.1 Cyclopropylcarbinyl Activated Precursors, 139\u003c\/p\u003e \u003cp\u003e5.2.2 Cyclopropyl Activated Precursors, 142\u003c\/p\u003e \u003cp\u003e5.2.3 Fragmentation of the Cyclopropane Precursors, 146\u003c\/p\u003e \u003cp\u003e5.2.4 Cooperatively Activated Cyclopropane Precursors, 147\u003c\/p\u003e \u003cp\u003e5.3 Formation of Carbonyl Groups, 151\u003c\/p\u003e \u003cp\u003e5.3.1 Cyclopropylcarbinyl Precursors, 151\u003c\/p\u003e \u003cp\u003e5.3.2 Cooperatively Activated Precursors, 156\u003c\/p\u003e \u003cp\u003e5.4 Retrosynthetic Account, 162\u003c\/p\u003e \u003cp\u003eReferences, 163\u003c\/p\u003e \u003cp\u003e\u003cb\u003e6 Cyclobutane Derivatives 167\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e6.1 Grandisol Syntheses, 167\u003c\/p\u003e \u003cp\u003e6.2 Cyclobutane Synthetic Intermediates, 169\u003c\/p\u003e \u003cp\u003e6.3 Retrosynthetic Account, 183\u003c\/p\u003e \u003cp\u003eReferences, 184\u003c\/p\u003e \u003cp\u003e\u003cb\u003e7 Cyclopentanes 187\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e7.1 Vinylcyclopropane–Cyclopentene Rearrangement, 187\u003c\/p\u003e \u003cp\u003e7.1.1 Cyclopropylcarbinyl Activated Precursors, 187\u003c\/p\u003e \u003cp\u003e7.1.2 Cooperatively Activated Precursors, 188\u003c\/p\u003e \u003cp\u003e7.2 Cycloaddition Reactions, 221\u003c\/p\u003e \u003cp\u003e7.2.1 Cyclopropylcarbinyl Activated Precursors, 221\u003c\/p\u003e \u003cp\u003e7.2.2 Cooperatively Activated Precursors, 221\u003c\/p\u003e \u003cp\u003e7.3 Modification of Substituents, 223\u003c\/p\u003e \u003cp\u003e7.3.1 N onactivated Cyclopropane Precursors, 223\u003c\/p\u003e \u003cp\u003e7.3.2 Cyclopropylcarbinyl Activated Precursors, 224\u003c\/p\u003e \u003cp\u003e7.3.3 Cooperatively Activated Precursors, 231\u003c\/p\u003e \u003cp\u003e7.3.4 Fragmentation Reactions, 245\u003c\/p\u003e \u003cp\u003e7.4 Retrosynthetic Account, 246\u003c\/p\u003e \u003cp\u003eReferences, 246\u003c\/p\u003e \u003cp\u003e\u003cb\u003e8 Cyclohexanes 251\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e8.1 Intramolecular Cyclization Reactions, 251\u003c\/p\u003e \u003cp\u003e8.2 Cycloaddition Reactions, 255\u003c\/p\u003e \u003cp\u003e8.3 Modification of Substituents, 269\u003c\/p\u003e \u003cp\u003e8.3.1 Cyclopropylcarbinyl Activated Precursors, 269\u003c\/p\u003e \u003cp\u003e8.3.2 Cyclopropyl Activated Precursors, 275\u003c\/p\u003e \u003cp\u003e8.3.3 Cooperatively Activated Precursors, 277\u003c\/p\u003e \u003cp\u003e8.4 Retrosynthetic Account, 282\u003c\/p\u003e \u003cp\u003eReferences, 283\u003c\/p\u003e \u003cp\u003e\u003cb\u003e9 Cycloheptanes 285\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e9.1 Divinylcyclopropane–Cycloheptadiene Rearrangement, 285\u003c\/p\u003e \u003cp\u003e9.2 Cycloaddition Reactions, 315\u003c\/p\u003e \u003cp\u003e9.3 Modification of Substituents, 318\u003c\/p\u003e \u003cp\u003e9.3.1 Nonactivated Cyclopropane Precursors, 318\u003c\/p\u003e \u003cp\u003e9.3.2 Cyclopropylcarbinyl Activated Precursors, 318\u003c\/p\u003e \u003cp\u003e9.3.3 Cyclopropyl Activated Precursors, 323\u003c\/p\u003e \u003cp\u003e9.3.4 Cooperatively Activated Precursors, 325\u003c\/p\u003e \u003cp\u003e9.4 Retrosynthetic Account, 329\u003c\/p\u003e \u003cp\u003eReferences, 330\u003c\/p\u003e \u003cp\u003e\u003cb\u003e10 Cyclooctanes and Larger Carbocycles 333\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e10.1 Cycloaddition Reactions, 333\u003c\/p\u003e \u003cp\u003e10.2 Modification of Substituents, 334\u003c\/p\u003e \u003cp\u003e10.2.1 Cyclopropylcarbinyl Activated Precursors, 334\u003c\/p\u003e \u003cp\u003e10.2.2 Cyclopropyl Activated Precursors, 338\u003c\/p\u003e \u003cp\u003e10.3 Retrosynthetic Account, 340\u003c\/p\u003e \u003cp\u003eReferences, 340\u003c\/p\u003e \u003cp\u003e\u003cb\u003e11 Heterocyclic Compounds 341\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e11.1 Intramolecular Cyclization Reactions, 341\u003c\/p\u003e \u003cp\u003e11.1.1 Nonactivated Cyclopropane Precursors, 341\u003c\/p\u003e \u003cp\u003e11.1.2 Cyclopropylcarbinyl Activated Precursors, 342\u003c\/p\u003e \u003cp\u003e11.1.3 Cyclopropyl Activated Precursors, 378\u003c\/p\u003e \u003cp\u003e11.1.4 Cooperatively Activated Precursors, 380\u003c\/p\u003e \u003cp\u003e11.2 Cycloaddition Reactions, 387\u003c\/p\u003e \u003cp\u003e11.2.1 Cyclopropylcarbinyl Activated Precursors, 387\u003c\/p\u003e \u003cp\u003e11.2.2 Cooperatively Activated Precursors, 390\u003c\/p\u003e \u003cp\u003e11.3 Modification of Substituents, 400\u003c\/p\u003e \u003cp\u003e11.3.1 Cyclopropylcarbinyl Activated Substrates, 400\u003c\/p\u003e \u003cp\u003e11.3.2 Cyclopropyl Activated Substrates, 402\u003c\/p\u003e \u003cp\u003e11.3.3 Cooperatively Activated Substrates, 402\u003c\/p\u003e \u003cp\u003e11.4 Retrosynthetic Account, 409\u003c\/p\u003e \u003cp\u003eReferences, 410\u003c\/p\u003e \u003cp\u003eCONCLUSION 415\u003c\/p\u003e \u003cp\u003eAUTHOR Index 417\u003c\/p\u003e \u003cb\u003eOleg Kulinkovich\u003c\/b\u003e was the head of the Department of Organic Chemistry from 1993-2003 and the head of the Laboratory of Organoelement Synthesis at Belarusian State University and visiting professor at Tallinn University of Technology. His seminal work on titanium-catalyzed cyclopropanation of carboxylic esters with Grignard reagents bearing β-hydrogen atoms (Kulinkovich reaction) is very well-known. Dr. Kulinkovich has published several reviews and original articles on organic synthesis in leading international journals. \u003cp\u003eUsed in total synthesis of natural products and other complex molecules, cyclopropanes can be conveniently prepared with different approaches and used as intermediates to make target-directed organic transformations  more efficient. The synthetic potential of cyclopropane derivatives is often overlooked but is nonetheless universal and could be more efficient than standard approaches.\u003cbr\u003e\u003cbr\u003eThis book provides a comprehensive review of cyclopropanes – their properties, preparation, synthesis, and applications. It includes comprehensive references and synopses of review articles on  experimental data and theoretical interpretations of the geometry of cyclopropanes and also discusses typical transformations of substituted cyclopropanes, derivatives, and intermediates, with emphasis on highly selective transformations of easily available cyclopropane precursors. The author provides a detailed description of successful applications of cyclopropane approaches in target-oriented syntheses classified by the class of the target structures and  transformation type, and mode of the activation of the cyclopropane ring toward its cleavage.\u003c\/p\u003e \u003cp\u003e\u003cbr\u003eOverall, the book stresses universality, experimental efficiency, and strategic importance of synthetic methodologies based on an efficient preparation of cyclopropane derivatives and their involvement in smooth ring opening or fragmentation reactions with inexpensive reagents. A valuable guide for practicing chemists, this book offers key features that include:\u003cbr\u003e\u003cbr\u003e•          A resource to help readers better understand cyclopropane applications for the efficient realization of synthetically important organic transformations and popular experimental procedures\u003cbr\u003e•          New developments and up-to-date information that will lead to original methodologies for complex organic synthesis\u003cbr\u003e•          Focus on the synthetic potential of cyclopropane applications, as well on their planning by retrosynthetic analysis\u003c\/p\u003e","brand":"Wiley","offers":[{"title":"Default Title","offer_id":47989020393701,"sku":"NP9781118057438","price":196.95,"currency_code":"USD","in_stock":false}],"thumbnail_url":"\/\/cdn.shopify.com\/s\/files\/1\/1842\/7735\/files\/9781118057438.jpg?v=1761782466","url":"https:\/\/k12savings.com\/products\/cyclopropanes-in-organic-synthesis-isbn-9781118057438","provider":"K12savings","version":"1.0","type":"link"}