Meta tags:

Headings (most frequently used words):

sakurai, reaction, contents, mechanism, literature, of, historic, interest, references, external, links,

Text of the page (most frequently used words):
the (40), #reaction (25), #sakurai (21), hosomi (11), and (10), edit (8), doi (8), allylsilanes (8), wikipedia (7), from (6), carbon (6), addition (6), akira (6), chemistry (6), chemical (6), ketone (6), page (5), with (5), reactions (5), organic (5), issn (5), hideki (5), tetrachloride (5), silicon (5), contents (4), search (4), this (4), links (4), allylation (4), 1021 (4), electrophilic (4), beta (4), titanium (4), shown (4), lewis (4), hide (4), move (4), sidebar (4), view (3), using (3), org (3), general (3), journal (3), american (3), society (3), fleming (3), ian (3), related (3), enones (3), allyl (3), group (3), 1976 (3), carbonyl (3), strong (3), allyltrimethylsilane (3), such (3), figure (3), mechanism (3), here (3), tools (3), main (3), languages (2), toggle (2), table (2), contact (2), about (2), privacy (2), policy (2), terms (2), may (2), wikimedia (2), use (2), commons (2), was (2), june (2), categories (2), ignored (2), short (2), description (2), wikidata (2), nucleophilic (2), retrieved (2), external (2), 0002 (2), 7863 (2), 124 (2), bibcode (2), september (2), help (2), cite (2), isbn (2), 1016 (2), allylstannanes (2), systems (2), synthetic (2), references (2), compounds (2), conjugate (2), alpha (2), 941 (2), letters (2), syntheses (2), presence (2), 4039 (2), literature (2), historic (2), interest (2), secondary (2), carbocation (2), intermediate (2), are (2), effect (2), compound (2), functional (2), groups (2), has (2), been (2), acid (2), also (2), other (2), showing (2), acids (2), portal (2), appearance (2), upload (2), file (2), changes (2), history (2), read (2), article (2), log (2), create (2), account (2), donate (2), menu (2), add, topic, mobile, cookie, statement, statistics, developers, code, conduct, legal, safety, contacts, disclaimers, text, available, under, additional, apply, site, you, agree, registered, trademark, non, profit, organization, foundation, inc, creative, attribution, sharealike, license, rendered, parsoid, last, edited, 2026, utc, hidden, cs1, errors, periodical, dmy, dates, december, 2022, matches, articles, name, bond, forming, https, index, php, title, sakurai_reaction, oldid, 1360734038, homepage, www, yamasaki, shingo, fujii, kunihiko, wada, reiko, kanai, motomu, shibasaki, masakatsu, 2002, catalytic, allyltrimethoxysilane, 6537, 12047165, pmid, ja0262582, 2002jachs, 6536y, 6536, 2019, work, book, january, 1991, trost, barry, eds, pergamon, 593, 9780080523491, b978, 052349, 00041, 563, dunoguès, jacques, smithers, roger, 2004, substitution, vinylsilanes, 575, 9780471264187, 1002, 0471264180, or037, 1988, characteristics, their, applications, versatile, equivalents, 206, 0001, 4842, ar00149a004, 200, accounts, research, march, 1977, organosilicon, new, method, stereoselective, introduction, angular, fused, cyclic, 1675, ja00447a080, 1977jachs, 1673h, 1673, endo, masahiko, 942, 0366, 7022, 1246, intermediates, homoallyl, ethers, acetals, promoted, akíra, unsaturated, alcohols, 1298, 0040, s0040, 78044, 1295, tetrahedron, kumada, makoto, 1969, trichloromethyl, radicals, alkenylsilanes, 1768, jo01258a052, 1764, displayed, scheme, proposed, give, carbocations, high, energy, however, stabilized, substituent, form, hyperconjugation, containing, two, different, given, treated, according, principle, first, activates, which, then, undergoes, attack, electrons, allylic, silane, plays, key, role, stabilizing, position, applicable, for, where, usually, seen, cinnamoyl, follows, same, previous, enone, alcl, all, effective, promoting, involves, via, silyl, carbocationic, shift, tin, boron, trifluoride, known, catalyzed, achieves, results, similar, grignard, reagent, electrophiles, rxno, 0000443, ontology, rsc, identifiers, type, named, after, free, encyclopedia, item, projects, printable, version, download, pdf, print, export, switch, legacy, parser, get, shortened, url, information, permanent, link, what, actions, english, talk, українська, română, nederlands, 한국어, 日本語, français, فارسی, español, deutsch, čeština, top, personal, special, pages, recent, community, learn, contribute, random, current, events, navigation, jump, content,

Text of the page (random words):
sakurai reaction wikipedia jump to content main menu main menu move to sidebar hide navigation main page contents current events random article about wikipedia contact us contribute help learn to edit community portal recent changes upload file special pages search search appearance donate create account log in personal tools donate create account log in contents move to sidebar hide top 1 mechanism 2 literature of historic interest 3 references 4 external links toggle the table of contents sakurai reaction 11 languages čeština deutsch español فارسی français 日本語 한국어 nederlands română українська 中文 edit links article talk english read edit view history tools tools move to sidebar hide actions read edit view history general what links here related changes upload file permanent link page information cite this page get shortened url switch to legacy parser print export download as pdf printable version in other projects wikimedia commons wikidata item appearance move to sidebar hide from wikipedia the free encyclopedia chemical reaction sakurai reaction named after hideki sakurai akira hosomi reaction type addition reaction identifiers organic chemistry portal hosomi sakurai reaction rsc ontology id rxno 0000443 the sakurai reaction also known as the hosomi sakurai reaction is the chemical reaction of carbon electrophiles such as a ketone shown here with allyltrimethylsilane catalyzed by strong lewis acids 1 2 3 the reaction achieves results similar to the addition of an allyl grignard reagent to the carbonyl the sakurai reaction strong lewis acids such as titanium tetrachloride boron trifluoride tin tetrachloride and alcl et 2 are all effective in promoting the sakurai reaction the reaction involves electrophilic allyl shift via a beta silyl carbocationic intermediate the beta silicon effect 4 mechanism edit figure 1 sakurai reaction showing allylation of a ketone figure 2 sakurai reaction showing allylation of an enone allylation of a carbonyl ketone compound containing a ketone group and two different functional groups has been shown in the given reaction the electrophilic compound carbon with a ketone group is treated with titanium tetrachloride a strong lewis acid and allyltrimethylsilane according to the general principle the lewis acid first activates the electrophilic carbon in presence of allyltrimethylsilane which then undergoes nucleophilic attack from electrons on the allylic silane 5 the silicon plays the key role in stabilizing the carbocation of carbon at the β position the sakurai reaction is also applicable for other functional groups such as enones where conjugate addition is usually seen in figure 2 the sakurai reaction has been shown using a cinnamoyl ketone this reaction follows the same mechanism as the previous reaction shown here as displayed in the scheme the sakurai reaction is proposed to give a secondary carbocation intermediate secondary carbocations are high in energy however it is stabilized by the silicon substituent β silicon effect a form of silicon hyperconjugation literature of historic interest edit sakurai hideki hosomi akira kumada makoto 1969 addition of trichloromethyl radicals to alkenylsilanes the journal of organic chemistry 36 4 1764 1768 doi 10 1021 jo01258a052 hosomi akíra sakurai hideki 1976 syntheses of γ δ unsaturated alcohols from allylsilanes and carbonyl compounds in the presence of titanium tetrachloride tetrahedron letters 17 16 1295 1298 doi 10 1016 s0040 4039 00 78044 0 issn 0040 4039 hosomi akira endo masahiko sakurai hideki 5 september 1976 allylsilanes as synthetic intermediates ii syntheses of homoallyl ethers from allylsilanes and acetals promoted by titanium tetrachloride chemistry letters 5 9 941 942 doi 10 1246 cl 1976 941 issn 0366 7022 hosomi akira sakurai hideki 1 march 1977 chemistry of organosilicon compounds 99 conjugate addition of allylsilanes to alpha beta enones a new method of stereoselective introduction of the angular allyl group in fused cyclic alpha beta enones journal of the american chemical society 99 5 1673 1675 bibcode 1977jachs 99 1673h doi 10 1021 ja00447a080 issn 0002 7863 references edit hosomi akira 1 may 1988 characteristics in the reactions of allylsilanes and their applications to versatile synthetic equivalents accounts of chemical research 21 5 200 206 doi 10 1021 ar00149a004 issn 0001 4842 fleming ian dunoguès jacques smithers roger 2004 the electrophilic substitution of allylsilanes and vinylsilanes organic reactions american chemical society pp 57 575 doi 10 1002 0471264180 or037 02 isbn 9780471264187 fleming ian 1 january 1991 allylsilanes allylstannanes and related systems in trost barry m fleming ian eds 2 2 allylsilanes allylstannanes and related systems pergamon pp 563 593 doi 10 1016 b978 0 08 052349 1 00041 x isbn 9780080523491 cite book work ignored help hosomi sakurai reaction organic chemistry org retrieved 1 september 2019 yamasaki shingo fujii kunihiko wada reiko kanai motomu shibasaki masakatsu 1 june 2002 a general catalytic allylation using allyltrimethoxysilane journal of the american chemical society 124 23 6536 6537 bibcode 2002jachs 124 6536y doi 10 1021 ja0262582 issn 0002 7863 pmid 12047165 external links edit hosomi sakurai reaction www organic chemistry org akira hosomi homepage retrieved from https en wikipedia org w index php title sakurai_reaction oldid 1360734038 categories nucleophilic addition reactions carbon carbon bond forming reactions name reactions hidden categories articles with short description short description matches wikidata use dmy dates from december 2022 cs1 errors periodical ignored this page was last edited on 23 june 2026 at 07 28 utc page was rendered with parsoid text is available under the creative commons attribution sharealike 4 0 license additional terms may apply by using this site you agree to the terms of use and privacy policy wikipedia is a registered trademark of the wikimedia foundation inc a non profit organization privacy policy about wikipedia disclaimers contact wikipedia legal safety contacts code of conduct developers statistics cookie statement mobile view search search toggle the table of contents sakurai reaction 11 languages add topic