NDLI: A Versatile Synthetic Platform Based on Bicyclo[4.1.0]heptenes

Content Provider	Springer Nature Link
Author	Chung, Young Keun Chang, Kyung Mi Kim, Ju Hyun
Copyright Year	2013
Abstract	Bicyclo[4.1.0]heptenes, which are readily accessible molecules via the transition metal-catalyzed cycloisomerization of 1,6-enynes, and have served as useful building blocks in organic synthesis. These molecules can undergo a variety of ring-opening reactions given that the release of the cyclopropyl ring strain (27.5 kcal/mol) may serve as a thermodynamic driving force for reactions, and the double bond within the skeleton can afford the kinetic opportunity to initiate the ring-opening via a coordination to a metal species. Even though the chemistry of the cyclopropyl group has been widely explored in organic chemistry, less attention has been paid to the chemistry of bicyclo[4.1.0]heptenes. However, during the past 5 years, we have been engaged in the exploration of the chemistry of bicyclo[4.1.0]heptenes. This review describes the chemistry developed in our laboratory. Depending upon the position, number, and identity of the substituent(s), the identity of the tether group, and the nature of the catalytic system, bicyclo[4.1.0]heptenes can undergo a variety of transformations. Our studies have revealed the reaction patterns of bicyclo[4.1.0]heptenes which include thermal reactions, nucleophilic addition, and rhodium-catalyzed reactions, that can proceed both with and without opening of the cyclopropyl ring. The chemistry described in this review can be used to produce a variety of new compounds such as 2,4-pentadienals, 3-methylene-4-vinylcyclohex-1-enes, bicyclo[3.2.2]nonadienes, 1,6,7,9a-tetrahydrocyclohepta[c] pyrans and -pyridines, hexahydroisoquinolines, 4-oxa-6-azatricyclo[3.3.0.0$^{2,8}$]octanes, and heterotricyclo[3.3.1.0$^{2,8}$]nonanes.
Starting Page	15
Ending Page	32
Page Count	18
File Format	PDF
ISSN	15741443
Journal	Journal of Inorganic and Organometallic Polymers and Materials
Volume Number	24
Issue Number	1
e-ISSN	15741451
Language	English
Publisher	Springer US
Publisher Date	2013-09-27
Publisher Place	Boston
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Bicyclo[4.1.0]heptenes Cyclopropane derivatives Cycloisomerization Inorganic Chemistry Organic Chemistry Polymer Sciences
Content Type	Text
Resource Type	Article
Subject	Materials Chemistry Polymers and Plastics

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