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2 p bromophenyl 9 07 4 96 n a n a 2 3 dimethyl 3 54 1 93 12 3 18 cis 1 methyl 0 18 0 10 n a n a trans 1 methyl 0 69 0 38 n a n a 1 2 dimethylene cyclohexane 24 7 13 5 11 4 16 2 methyl 1 1 4 4 d 4 1 96 n a n a n a more recently a 2002 study by monnat vogel and sordo measured the kinetics of addition of sulfur dioxide to 1 2 dimethylidenecycloalkanes an interesting point presented in this paper is that the reaction of 1 2 dimethylidene cyclohexane 1 with sulfur dioxide can give two different products depending on reaction conditions the reaction produces the corresponding sulfine 2 through a hetero diels alder reaction under kinetic control 60 c but under thermodynamic control 40 c the reaction produces the corresponding sulfolene 3 through a cheletropic reaction the activation enthalpy for the hetero diels alder reaction is about 8 kj mol smaller than that for the corresponding cheletropic reaction the sulfolene is about 40 kj mol more stable than the isometric sulfine in ch 2 cl 2 so 2 solution 6 the authors were able to experimentally determine a rate law at 261 2 k for the reaction of 1 2 dimethylidene cyclohexane with sulfur dioxide to give the corresponding sulfolene the reaction was first order in 1 2 dimethylidene cyclohexane but second order in sulfur dioxide see below this confirmed a prediction based on high level ab initio quantum calculations using computational methods the authors proposed a transition structure for the cheletropic reaction of 1 2 dimethylidene cyclohexane with sulfur dioxide 6 the reaction is second order in sulfur dioxide because another molecule of sulfur dioxide likely binds to the transition state to help stabilize it 7 similar results were found in a 1995 study by suarez sordo and sordo which used ab initio calculations to study the kinetic and thermodynamic control of the reaction of sulfur dioxide with 1 3 dienes 4 d 3 d t k 2 1 so 2 2 displaystyle frac d 3 dt k_ 2 1 ce so2 2 solvent effects edit cheletropic reaction studied in various solvents the effect of the solvent of the cheletropic reaction of 3 4 dimethyl 2 5 dihydrothiophen 1 1 dioxide shown at right was kinetically investigated in 14 solvents the reaction rate constants of the forward and reverse reaction in addition to the equilibrium constants were found to be linearly correlated with the e t 30 solvent polarity scale reactions were done at 120 c and were studied by 1h nmr spectroscopy of the reaction mixture the forward rate k 1 was found to decrease by a factor of 4 5 going from cyclohexane to methanol the reverse rate k 1 was found to increase by a factor of 53 going from cyclohexane to methanol while the equilibrium constant k eq decreased by a factor of 140 it is suggested that there is a change of the polarity during the activation process as evidenced by correlations between the equilibrium and kinetic data the authors remark that the reaction appears to be influenced by the polarity of the solvent and this can be explained by the change in the dipole moments when going from reactant to transition state to product the authors also state that the cheletropic reaction doesn t seem to be influenced by either solvent acidity or basicity the results of this study lead the authors to expect the following behaviors 1 the change in the solvent polarity will influence the rate less than the equilibrium 2 the rate constants will be characterized by opposite effect on the polarity k 1 will slightly decrease with the increase of e t 30 and k 1 will increase under the same conditions 3 the effect on k 1 will be larger than on k 1 8 carbene additions to alkenes edit addition of a carbene to an alkene to form a cyclopropane one of the most synthetically important cheletropic reactions is the addition of a singlet carbene to an alkene to make a cyclopropane see figure at left 1 a carbene is a neutral molecule containing a divalent carbon with six electrons in its valence shell due to this carbenes are highly reactive electrophiles and generated as reaction intermediates 9 a singlet carbene contains an empty p orbital and a roughly sp 2 hybrid orbital that has two electrons singlet carbenes add stereospecifically to alkenes and alkene stereochemistry is retained in the cyclopropane product 1 the mechanism for addition of a carbene to an alkene is a concerted 2 1 cycloaddition see figure carbenes derived from chloroform or bromoform can be used to add cx 2 to an alkene to give a dihalocyclopropane while the simmons smith reagent adds ch 2 10 a the orbitals for singlet carbenes b non linear approach of a carbene sp 2 orbital and b carbene p orbital interaction of the filled carbene orbital with the alkene π system creates a four electron system and favors a non linear approach it is also favorable to mix the carbene empty p orbital with the filled alkene π orbital favorable mixing occurs through a non linear approach see figure at right however while theory clearly favors a non linear approach there are no obvious experimental implications for a linear vs non linear approach 1 references edit 1 2 3 4 5 6 eric v anslyn and dennis a dougherty modern physical organic chemistry university science books 2006 chelotropic reaction iupac goldbook ian fleming frontier orbitals and organic chemistry reactions wiley 1976 1 2 suarez d sordo t l sordo j a 1995 a comparative analysis of the mechanisms of cheletropic and diels alder reactions of 1 3 dienes with sulfur dioxide kinetic and thermodynamic controls j org chem 60 9 2848 2852 doi 10 1021 jo00114a039 isaacs n s laila a a r 1976 rates of addition of sulphur dioxide to some 1 3 dienes tetrahedron lett 17 9 715 716 doi 10 1016 s0040 4039 00 74605 3 1 2 monnat f vogel p sordo j a 2002 hetero diels alder and cheletropic additions of sulfur dioxide to 1 2 dimethylidenecycloalkanes determination of thermochemical and kinetics parameters for reactions in solution and comparison with estimates from quantum calculations helv chim acta 85 3 712 732 doi 10 1002 1522 2675 200203 85 3 712 aid hlca712 3 0 co 2 5 fernandez t sordo j a monnat f deguin b vogel p 1998 sulfur dioxide promotes its hetero diels alder and cheletropic additions to 1 2 dimethylidenecyclohexane j am chem soc 120 50 13276 13277 bibcode 1998jachs 12013276f doi 10 1021 ja982565p desimoni g faita g garau s righetti p 1996 solvent effect in pericyclic reactions x the cheletropic reaction tetrahedron 52 17 6241 6248 doi 10 1016 0040 4020 96 00279 7 john mcmurry organic chemistry 6th ed thomson 2004 robert b grossman the art of writing reasonable organic reaction mechanisms springer 2003 v t e topics in organic reactions addition reaction elimination reaction polymerization reagents rearrangement reaction redox reaction regioselectivity stereoselectivity stereospecificity substitution reaction a value alpha effect annulene anomeric effect antiaromaticity aromatic ring current aromaticity baird s rule baker nathan effect baldwin s rules bema hapothle beta silicon effect bicycloaromaticity bredt s rule bürgi dunitz angle catalytic resonance theory charge remote fragmentation charge transfer complex clar s rule conformational isomerism conjugated system conrotatory and disrotatory curtin hammett principle dynamic binding chemistry edwards equation effective molarity electromeric effect electron rich electron withdrawing group electronic effect electrophile evelyn effect flippin lodge angle free energy relationship grunwald winstein equation hammett acidity function hammett equation george s hammond hammond s postulate homoaromaticity hückel s rule hyperconjugation inductive effect kinetic isotope effect lfer solvent coefficients data page marcus theory markovnikov s rule möbius aromaticity möbius hückel concept more o ferrall jencks plot negative hyperconjugation neighbouring group participation 2 norbornyl cation nucleophile kennedy j p orton passive binding phosphaethynolate polar effect polyfluorene ring strain σ aromaticity spherical aromaticity spiroaromaticity steric effects superaromaticity swain lupton equation taft equation thorpe ingold effect vinylogy walsh diagram woodward hoffmann rules woodward s rules y aromaticity yukawa tsuno equation zaitsev s rule σ bishomoaromaticity list of organic reactions carbon carbon bond forming reactions acetoacetic ester synthesis acyloin condensation aldol condensation aldol reaction alkane metathesis alkyne metathesis alkyne trimerisation alkynylation allan robinson reaction arndt eistert reaction auwers synthesis aza baylis hillman reaction barbier reaction barton kellogg reaction baylis hillman reaction benary reaction bergman cyclization biginelli reaction bingel reaction blaise ketone synthesis blaise reaction blanc chloromethylation bodroux chichibabin aldehyde synthesis bouveault aldehyde synthesis bucherer bergs reaction buchner ring expansion cadiot chodkiewicz coupling carbonyl allylation carbonyl olefin metathesis castro stephens coupling chan rearrangement chan lam coupling claisen condensation claisen rearrangement claisen schmidt condensation combes quinoline synthesis corey fuchs reaction corey house synthesis coupling reaction cross coupling reaction cross dehydrogenative coupling cross coupling partner dakin west reaction darzens reaction diels alder reaction doebner reaction wulff dötz reaction ene reaction enyne metathesis ethenolysis favorskii reaction ferrier carbocyclization friedel crafts reaction fujimoto belleau reaction fujiwara moritani reaction fukuyama coupling gabriel colman rearrangement gattermann reaction glaser coupling grignard reaction grignard reagent hammick reaction heck reaction henry reaction heterogeneous metal catalyzed cross coupling high dilution principle hiyama coupling homologation reaction horner wadsworth emmons reaction hydrocyanation hydrovinylation hydroxymethylation ivanov reaction johnson corey chaykovsky reaction julia olefination julia kocienski olefination kauffmann olefination knoevenagel condensation knorr pyrrole synthesis kolbe schmitt reaction kowalski ester homologation kulinkovich reaction kumada coupling liebeskind srogl coupling malonic ester synthesis mannich reaction mcmurry reaction meerwein arylation methylenation michael reaction minisci reaction mizoroki heck vs reductive heck nef isocyanide reaction nef synthesis negishi coupling nierenstein reaction nitro mannich reaction nozaki hiyama kishi reaction olefin conversion technology olefin metathesis palladium nhc complex passerini reaction peterson olefination pfitzinger reaction piancatelli rearrangement pinacol coupling reaction prins reaction quelet reaction ramberg bäcklund reaction rauhut currier reaction reformatsky reaction reimer tiemann reaction rieche formylation ring closing metathesis robinson annulation sakurai reaction seyferth gilbert homologation shapiro reaction sonogashira coupling stetter reaction stille reaction stollé synthesis stork enamine alkylation suzuki reaction takai olefination thermal rearrangement of aromatic hydrocarbons thorpe reaction ugi reaction ullmann reaction wagner jauregg reaction weinreb ketone synthesis wittig reaction wurtz reaction wurtz fittig reaction zincke suhl reaction homologation reactions arndt eistert reaction hooker reaction kiliani fischer synthesis kowalski ester homologation methoxymethylenetriphenylphosphorane seyferth gilbert homologation wittig reaction olefination reactions bamford stevens reaction barton kellogg reaction boord olefin synthesis chugaev elimination cope reaction corey winter olefin synthesis dehydrohalogenation elimination reaction grieco elimination hofmann elimination horner wadsworth emmons reaction hydrazone iodination julia olefination julia kocienski olefination kauffmann olefination mcmurry reaction peterson olefination ramberg bäcklund reaction shapiro reaction takai olefination wittig reaction carbon heteroatom bond forming reactions azo coupling bartoli indole synthesis boudouard reaction cadogan sundberg indole synthesis diazonium compound esterification grignard reagent haloform reaction hegedus indole synthesis hurd mori 1 2 3 thiadiazole synthesis kharasch sosnovsky reaction knorr pyrrole synthesis leimgruber batcho indole synthesis mukaiyama hydration nenitzescu indole synthesis oxymercuration reaction reed reaction schotten baumann reaction ullmann condensation williamson ether synthesis yamaguchi esterification degradation reactions barbier wieland degradation bergmann degradation edman degradation emde degradation gallagher hollander degradation hofmann rearrangement hooker reaction isosaccharinic acid marker degradation ruff degradation strecker degradation von braun amide degradation weerman degradation wohl degradation organic redox reactions acyloin condensation adkins peterson reaction akabori amino acid reaction alcohol oxidation algar flynn oyamada reaction amide reduction andrussow process angeli rimini reaction aromatization autoxidation baeyer villiger oxidation barton mccombie deoxygenation bechamp reduction benkeser reaction bergmann degradation birch reduction bohn schmidt reaction bosch reaction bouveault blanc reduction boyland sims oxidation cannizzaro reaction carbonyl reduction clemmensen reduction collins oxidation corey itsuno reduction corey kim oxidation corey winter olefin synthesis criegee oxidation dakin oxidation davis oxidation deoxygenation dess martin oxidation dna oxidation elbs persulfate oxidation emde degradation eschweiler clarke reaction étard reaction fischer tropsch process fleming tamao oxidation fukuyama reduction ganem oxidation glycol cleavage griesbaum coozonolysis grundmann aldehyde synthesis haloform reaction hydrogenation hydrogenolysis hydroxylation jones oxidation kiliani fischer synthesis kolbe electrolysis kornblum oxidation kornblum delamare rearrangement leuckart reaction ley oxidation lindgren oxidation lipid peroxidation lombardo methylenation luche reduction markó lam deoxygenation mcfadyen stevens reaction meerwein ponndorf verley reduction methionine sulfoxide miyaura borylation mozingo reduction noyori asymmetric hydrogenation omega oxidation oppenauer oxidation oxygen rebound mechanism ozonolysis parikh doering oxidation pinnick oxidation prévost reaction reduction of nitro compounds reductive amination riley oxidation rosenmund reduction rubottom oxidation sabatier reaction sarett oxidation selenoxide elimination shapiro reaction sharpless asymmetric dihydroxylation epoxidation of allylic alcohols sharpless epoxidation sharpless oxyamination stahl oxidation staudinger reaction stephen aldehyde synthesis swern oxidation transfer hydrogenation wacker process wharton reaction whiting reaction wohl aue reaction wolff kishner reduction wolffenstein böters reaction zinin reaction rearrangement reactions 1 2 rearrangement 1 2 wittig rearrangement 2 3 sigmatropic rearrangement 2 3 wittig rearrangement achmatowicz reaction alkyne zipper reaction allen millar trippett rearrangement allylic rearrangement alpha ketol rearrang...