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In organic chemistry, the Michael reaction or Michael 1,4 addition is a reaction between a Michael donor (an enolate or other nucleophile) and a Michael acceptor (usually an α,β-unsaturated carbonyl) to produce a Michael adduct by creating a carbon-carbon bond at the acceptor's β-carbon. It belongs to the larger class of conjugate additions and is widely used for the mild formation of carbon-carbon bonds. The Michael addition is an important atom-economical method for diastereoselective and enantioselective C–C bond formation, and many asymmetric variants existIn this general Michael addition scheme, either or both of R and R' on the nucleophile (the Michael donor) represent electron-withdrawing substituents such as acyl, cyano, nitro, or sulfone groups, which make the adjacent methylene hydrogen acidic enough to form a carbanion when reacted with the base, B:. For the alkene (the Michael acceptor), the R" substituent is usually a carbonyl, which makes the compound an α,β-unsaturated carbonyl compound (either an enone or an enal), or R" may be any electron withdrawing group. Definition As originally defined by Arthur Michael, the reaction is the addition of an enolate of a ketone or aldehyde to an α,β-unsaturated carbonyl compound at the β carbon. The current definition of the Michael reaction has broadened to include nucleophiles other than enolates. Some examples of nucleophiles include doubly stabilized carbon nucleophiles such as beta-ketoesters, malonates, and beta-cyanoesters. The resulting product contains a highly useful 1,5-dioxygenated pattern. Non-carbon nucleophiles such as water, alcohols, amines, and enamines can also react with an α,β-unsaturated carbonyl in a 1,4-addition.Some authors have broadened the definition of the Michael addition to essentially refer to any 1,4-addition reaction of α,β-unsaturated carbonyl compounds. Others, however, insist that such a usage is an abuse of terminology, and limit the Michael addition to the formation of carbon–carbon bonds through the addition of carbon nucleophiles. The terms oxa-Michael reaction and aza-Michael reaction have been used to refer to the 1,4-addition of oxygen and nitrogen nucleophiles, respectively. The Michael reaction has also been associated with 1,6-addition reactions. Mechanism In the reaction mechanism, there is 1 as the nucleophile: Deprotonation of 1 by a base leads to carbanion 2, stabilized by its electron-withdrawing groups. Structures 2a to 2c are three resonance structures that can be drawn for this species, two of which have enolate ions. This nucleophile reacts with the electrophilic alkene 3 to form 4 in a conjugate addition reaction. Finally, enolate 4 abstracts a proton from protonated base (or solvent) to produce 5. The reaction is dominated by orbital, rather than electrostatic, considerations. The HOMO of stabilized enolates has a large coefficient on the central carbon atom while the LUMO of many alpha, beta unsaturated carbonyl compounds has a large coefficient on the beta carbon. Thus, both reactants can be considered soft. These polarized frontier orbitals are of similar energy, and react efficiently to form a new carbon–carbon bond.Like the aldol addition, the Michael reaction may proceed via an enol, silyl enol ether in the Mukaiyama–Michael addition, or more usually, enolate nucleophile. In the latter case, the stabilized carbonyl compound is deprotonated with a strong base (hard enolization) or with a Lewis acid and a weak base (soft enolization). The resulting enolate attacks the activated olefin with 1,4-regioselectivity, forming a carbon–carbon bond. This also transfers the enolate to the electrophile. Since the electrophile is much less acidic than the nucleophile, rapid proton transfer usually transfers the enolate back to the nucleophile if the product is enolizable; however, one may take advantage of the new locus of nucleophilicity if a suitable electrophile is pendant. Depending on the relative acidities of the nucleophile and product, the reaction may be catalytic in base. In most cases, the reaction is irreversible at low temperature. History The research done by Arthur Michael in 1887 at Tufts University was prompted by an 1884 publication by Conrad & Kuthzeit on the reaction of ethyl 2,3-dibromopropionate with diethyl sodiomalonate forming a cyclopropane derivative (now recognized as involving two successive substitution reactions). Michael was able to obtain the same product by replacing the propionate by 2-bromacrylic acid ethylester and realized that this reaction could only work by assuming an addition reaction to the double bond of the acrylic acid. He then confirmed this assumption by reacting diethyl malonate and the ethyl ester of cinnamic acid forming the first Michael adduct: In the same year Rainer Ludwig Claisen claimed priority for the invention. He and T. Komnenos had observed addition products to double bonds as side-products earlier in 1883 while investigating condensation reactions of malonic acid with aldehydes. However, according to biographer Takashi Tokoroyama, this claim is without merit. Asymmetric Michael reaction Researchers have expanded the scope of Michael additions to include elements of chirality via asymmetric versions of the reaction. The most common methods involve chiral phase transfer catalysis, such as quaternary ammonium salts derived from the Cinchona alkaloids; or organocatalysis, which is activated by enamine or iminium with chiral secondary amines, usually derived from proline.In the reaction between cyclohexanone and β-nitrostyrene sketched below, the base proline is derivatized and works in conjunction with a protic acid such as p-toluenesulfonic acid: Syn addition is favored with 99% ee. In the transition state believed to be responsible for this selectivity, the enamine (formed between the proline nitrogen and the cycloketone) and β-nitrostyrene are co-facial with the nitro group hydrogen bonded to the protonated amine in the proline side group. A well-known Michael reaction is the synthesis of warfarin from 4-hydroxycoumarin and benzylideneacetone first reported by Link in 1944: Several asymmetric versions of this reaction exist using chiral catalysts. Examples Classical examples of the Michael reaction are the reaction between diethyl malonate (Michael donor) and diethyl fumarate (Michael acceptor), that of diethyl malonate and mesityl oxide (forming Dimedone), that of diethyl malonate and methyl crotonate, that of 2-nitropropane and methyl acrylate, that of ethyl phenylcyanoacetate and acrylonitrile and that of nitropropane and methyl vinyl ketone.A classic tandem sequence of Michael and aldol additions is the Robinson annulation. Mukaiyama-Michael addition In the Mukaiyama–Michael addition, the nucleophile is a silyl enol ether and the catalyst is usually titanium tetrachloride: 1,6-Michael reaction The 1,6-Michael reaction proceeds via nucleophilic attack on the 𝛿 carbon of an α,β-γ{\displayst.... Discover the Anie Michaels popular books. Find the top 100 most popular Anie Michaels books.
Best Seller Anie Michaels Books of 2024
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The Holy Bible - King James Version
King JamesHoly Bible King James Version Few Sample Paragraphs from The Holy Bible eBook, Genesis (OT) 1 Gen. 1 IN the beginning God created the heaven and the earth. 2 And the earth was with...
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Become A Better Version of Yourself
Ben LeightonThis ebook contains golden nuggets on how to motivate, inspire and improve your current situation. It encompasses the holistic view of self improvement from mental& emotion...
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Alpha
Sybil BartelBillionaire. Mercenary. Navy SEAL. The Teams trained me to be a killer. War taught me to be ruthless. Then an illfated mission proved I was human. Combat wounded, cut loose by the ...
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A Green Kind of Witch
Sierra CrossCinderella crossed with Mean Girls.   That's what Hazel's daily existence feels like. Born to a family of elegant yet shallow Beige Witches, seventeen y...
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The Wonderful Wizard of Oz
L. Frank BaumAn Apple Books Classic edition. You’ve seen the iconic 1939 movie, but do you know about the talking field mice, the Winkies, and the Witch of the North that appear in the original...
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Rogue Alpha
Kimber WhiteOne touch made her crave him. But the pull of fate could be the path to ruin. College student Laura Prince lands a plum internship deep in the Michigan wilderness. When she discove...
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The Target
Lexy TimmsWhen you seek revenge be sure to dig two graves… Revenge was the only thing I had going for me. It kept me awake at night and drove me into desperate situations in dive bars across...
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Death at Hazel House
Betty Rowlands‘Riveting, can't put it down! I love this story… a wonderfully twisted tale of a crime that has more twists than I thought possible... fantastic.’ Goodreads Reviewer, 5 stars ...
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Dream Psychology
Sigmund FreudAn Apple Books Classic edition. Written by the founding father of psychoanalysis, Sigmund Freud’s 1899 book is the definitive text on learning to interpret dreams. Freud’s groundbr...
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Good Guy
Kate MeaderHe's a Special Forces veteran making his pro hockey debut. She's a dogged sports reporter determined to get a scoop. She's also his best friend's widow . . . Fa...
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The Four Loves
C. S. LewisThe Four Loves summarizes four kinds of human loveaffection, friendship, erotic love, and the love of God. Masterful without being magisterial, this book's wise, gentle, candi...
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Saltwater Cove
Amelia AddlerSecond chances...and the secrets that sabotage them. At 48 years old, Margie Clifton never expected to be starting her life all over again. But when her brother gifts her a propert...
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The Scarlet Letter
Nathaniel HawthorneAn Apple Books Classic edition. Hester Prynne lives in infamy. After committing adultery and bearing a child with a man whose name she refuses to divulge, the heroine of Nathaniel ...
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My Paper Heart
Magan VernonOne piece of paper can change everything After my parents received the letter I failed out of college, they didn't ask questions. They just sent me to work for my great aunt i...
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Enemies With Benefits
Roxie NoirI don’t love him. I don’t even like him. I just want him. Eli Loveless was my nemesis from the first day of kindergarten until we graduated high school. Everything I did, he had to...
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Law of Attraction
Jordan HollisHow to Finally Overcome the Hurdles of Manifesting Proven, effective and enjoyable ways to help you manifest faster… Right now, think of something that makes you successful. If you...
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Inception of Gold
Lexy TimmsThings are not as bad as they seem. They are worse. Being the personal assistant to a narcissistic actress who just happens to own the key to my family's undoing isn't ex...
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The Three Little Pigs
Mark LeskyClassic fairy tales, legends and folk stories in short version without violence retold with lovely illustrations in simple language. Perfect for reading aloud to small chi...
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Eternal
W.J. MayShe will fight for what is hers. When the king is murdered, Katerina, his only daughter, must flee for her life. She finds herself on a strange and dangerous path. Alone for the fi...
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The Cupcake Cottage
Jean OramNHL player Maverick Blades could fall in love with anyone... But he had to fall for a woman who falls under the Bro Code as untouchablehis best friend’s beautiful ex, DaisyMae Ray....
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Pretty Little Lies
Ivy ThornFour years ago, Nicolo Marchetti took my innocence. But he left me with something else Nicolo almost took everything from me. My virginity, my reputation, and very nearly my future...
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Never Enough
Lexy TimmsBe good enough never is... Anthony Accardi is a man on a mission: make his father's watch company a success while bringing in millions of dollars. To do that, he needs an assi...
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Becoming Lady Dalton
Carrie LomaxA dance of desire and deceit... In the glittering world of London's ton, Mrs. Viola Cartwright revels in her newfound freedom as a lady of leisureuntil a series of jewel theft...
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A Christmas Carol
Charles DickensAn Apple Books Classic edition. It’s Christmas Eve in Victorian England. While some families don’t know where their next meal will come from, Ebenezer Scrooge sits in his large hom...
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All Fired Up
Kathryn ShayCaptain Jarek Zenko, a war veteran and firefighter, meets Lacey Roth at a bar one night. They don’t share their real identities, even when they retreat to a hotel. When they meet t...
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Dracula
Bram StokerAn Apple Books Classic edition. Few characters have seized readers’ imaginations quite like Count Dracula of Transylvania, the hero of Bram Stoker’s classic. The 1897 novel put vam...
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The Odyssey
HomerAn Apple Books Classic edition. Homer’s eighthcentury epic poem is a companion to The Iliad . It tells the story of Odysseus, who journeys by ship for 10 years after the Trojan War...
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Salvation
Meghan O'FlynnIf you like mouthy detectives, serial killers, and suspenseful mysteries that don't quit, this chilling and actionpacked hardboiled detective series has you covered! Try this ...
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The Adventures of Sherlock Holmes
Arthur Conan DoyleAn Apple Books Classic You get not one, not two, but 25 gripping mysteries in Arthur Conan Doyle’s first of five collections of Sherlock Holmes short stories. Follow the brilliant ...
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The Count of Monte Cristo
Alexandre DumasAn Apple Books Classic edition. Alexandre Dumas’ classic paints a portrait of Edmond Dantès, a dark and calculating man who is willing to wait years to exact his perfect plan for r...
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Pride and Prejudice
Jane AustenAn Apple Books Classic edition. Jane Austen’s beloved classic opens with this witty and very memorable line: “It is a truth universally acknowledged, that a single man in possessio...
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Masters of Restraint
Ines JohnsonMy new boss is good at giving orders. But his latest demand is NSFW. Especially when his two business partners want in on our deal. My new boss My boss’s boss Their investor &#...
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Once Upon A One-Night Stand
Zoey LockeAt first sight, there was electrifying chemistry.  So why not go for it? After all, Lynx Grove, the city's most eligible bachelor, wants to claim her, at least for th...
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Holy Bible
The Church of Jesus Christ of Latter-day SaintsThe 2013 edition of the Holy Bible contains all of the study aids contained in the 1979 edition and includes revisions to the study aids, several new photos, updated maps, and adju...
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Teased by Fire
Molly O'HareFrom USA Today bestselling author Molly O’Hare comes an enemiestolovers, older brother’s best friend, romantic comedy with a curvy, antisocial, supernaturalobsessed, allyearround h...
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Man In The Water
Jon HillAn attempted murder. A missing spouse. And an international conspiracy that could change the world. Jack Green has always been skeptical of socalled facts. Though he's forced ...
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Silenced Girls
Roger Stelljes“ Wow wow wow!  Grips you in a choke hold and  does not let go … Oozes suspense and  bonechilling twists and turns .  Astonishing … One of those...
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Teach Me
Cassandra DeanFrom awardwinning author Cassandra Dean comes a tale where lessons of pleasure between a curious, sunshine widow and a dissolute, grumpy earl leads to passion and allconsuming love...
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Dark Psychology and Manipulation
Margaret MorrisonTHE MENTAL MANIPULATOR WILL NO LONGER KEEP SECRETS FROM YOU! Are you fed up with the wool being pulled over your eyes?Are you prepared to stand up to those who believe they can man...
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You Are Kind
Michael GordonA little kindness goes a long way. How can you help encourage your kids to be kind from a young age? Teach kindness to preschoolers Acts of kindness can be fun, easy, and make a ...
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The Seduction Series Boxset
Roxy Sloane“Sensual, thrilling and wild!”   Discover the bestselling series in one collection: THE SEDUCTION, THE BARGAIN, and THE INVITATION. Perfect for fans of Ana Huang, Sierra S...
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His Girl Next Door
Khardine GrayFrom USA Today Bestselling author Khardine Gray comes a sizzling hot single dad romance you won't want to miss. No strings attached fun with the ubergorgeous single d...
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A Bookshop to Die For
M.P. BlackDitching her fiancé at the altar, Alice Hartford bolts to her childhood hometown to reconnect with the last, happy remnant of her past: her mom's old bookstore. But the bookst...
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Finding Cinderella
Colleen Hoover#1 New York Times bestselling author of It Starts with Us and It Ends With Us writes a free novella about the search for happily ever after. A chance encounter in the dark leads ei...
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The Great Gatsby
F. Scott FitzgeraldAn Apple Books Classics edition. The Roaring Twenties are in full effect in F. Scott Fitzgerald’s riveting classic. Manabouttown Jay Gatsby seems to have it all, including loads of...
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Peace on Earth
Maia RossCrime never takes a holiday. Why should Irma? Irma Abercrombie is an energetic retiree with a shadowy past, a mean right hook, and a profound love of Christmas. Surrounded by seaso...
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Meditations
Emperor of Rome Marcus AureliusMeditations is a series of personal writings by Marcus Aurelius, Roman Emperor 161–180 CE, setting forth his ideas on Stoic philosophy.
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Always Yours
Claire RayeSome things are just meant to be... Ellen Somerville and Will McIntyre met by accident and under unusual circumstances. Getting sprayed by a skunk in a parking lot wouldn’t normall...
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Wuthering Heights
Emily BrontëAn Apple Books Classic edition. If you’ve only ever seen Wuthering Heights on screen, you may have an image of Catherine and Heathcliff as the ultimate starcrossed lovers. But that...
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The Icing on the Cake
Linda SeedShe’s a baker without a kitchen. He’s got a double oven to spare. It’s a recipe for success, until his mother starts stirring up trouble … Cassie Jordan has a sweet dream to open a...