| 词条 | Bicyclopropenyl | |||||||||||||||||||||||
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 426240665 | ImageFile = Bicycloprop-2-enyl.svg | ImageSize = 100px | ImageFile1 = 3,3'-bicyclopropenyl-from-xtal-1993-Mercury-3D-balls.png | PIN = 1,1'-Bi(cycloprop-2-ene) | OtherNames = 1,1'-Bi(cycloprop-2-en-1-yl) 3,3'-Bicyclopropenyl |Section1={{Chembox Identifiers | CASNo_Ref = {{cascite|changed|??}} | CASNo = 62595-44-2 | PubChem = 143919 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 126965 | SMILES = C\\1=C\\C/1C\\2/C=C/2 | InChI = 1/C6H6/c1-2-5(1)6-3-4-6/h1-6H | InChIKey = HVWGZGIZCKXHJV-UHFFFAOYAR | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/C6H6/c1-2-5(1)6-3-4-6/h1-6H | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = HVWGZGIZCKXHJV-UHFFFAOYSA-N | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = |Section2={{Chembox Properties | Formula = C6H6 | MolarMass = 78.1 g/mol | Appearance = | Density = | MeltingPtK = 198 | MeltingPt_notes = | BoilingPt = | Solubility = |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} Bicyclopropenyl (bicycloprop-2-enyl, C6H6) is an organic compound and one of several valence isomers of benzene. The molecule can be described as two coupled cyclopropene units. The positions of the alkene groups can vary and therefore two other isomers are known: bicycloprop-1,2-enyl and bicyclopropen-1-yl. The synthesis of all three isomers was reported in 1989 By Billups and Haley.[1][2] The 3,3 isomer was formed in two steps by reaction of 1,4-bis(trimethylsilyl)buta-1,3-diene with methyllithium and dichloromethane, introducing two cyclopropane rings into the molecule. The bis(2-chloro-3-(trimethylsilyl)cyclopropan-1-yl) formed is reacted with TBAF. In this latter reaction fluoride couples to the trimethylsilyl group, in the process forming the double bond and forcing the chlorine atom to leave as chloride. In presence of silver ions bicycloprop-2-enyl rearranges to Dewar benzene. The compound can also be trapped by cyclopentadiene. Above -10 °C it decomposes with polymerization. An X-ray crystal structure has been reported.[3] The bond length for the central bond is short by 1.503 Ångström (150.3 pm). The other two isomers are increasingly unstable. Bicycloprop-1-enyl can only be detected in trapping experiments.
References1. ^{{Cite journal| doi = 10.1002/anie.198917111| title = Bicycloprop-2-enyl (C6H6)| year = 1989| last1 = Billups | first1 = W. E.| last2 = Haley | first2 = M. M.| journal = Angewandte Chemie International Edition in English| volume = 28| issue = 12| pages = 1711 }} 2. ^{{Cite journal| doi = 10.1016/S0040-4020(01)89261-9| title = Synthesis of the bicyclopropenyls | first4 = D.| last4 = Bläser | first3 = R.| last3 = Boese | first2 = M.| year = 1994| last2 = m. Haley| last1 = Billups | first1 = W.| journal = Tetrahedron| volume = 50| issue = 36| pages = 10693–10700 }} 3. ^{{Cite journal| doi = 10.1021/ja00055a052| title = Structure and photoelectron spectrum of 3,3'-bicyclopropenyl| year = 1993| last1 = Boese | first1 = R.| last2 = Blaeser | first2 = D.| last3 = Gleiter | first3 = R.| last4 = Pfeifer | first4 = K. H.| last5 = Billups | first5 = W. E.| last6 = Haley | first6 = M. M.| journal = Journal of the American Chemical Society| volume = 115| issue = 2| pages = 743 }} 4. ^1 {{Cite journal| doi = 10.1016/S0166-1280(98)00189-4| title = Ab initio calculations of the heats of formation for (CH)6 isomers| year = 1998| last1 = Cheung | first1 = Y.| journal = Journal of Molecular Structure: THEOCHEM| volume = 454| pages = 17–20 }} 5. ^1 G2 level, isodesmic bond separation scheme 2 : Bicyclic compounds|Cyclopropenes |
|||||||||||||||||||||||
| 随便看 |
|
|||||||||||||||||||||||
开放百科全书收录14589846条英语、德语、日语等多语种百科知识，基本涵盖了大多数领域的百科知识，是一部内容自由、开放的电子版国际百科全书。