官能团最全转换

1、官能团最全转换 i5-7-gfedcbaedcbaihgfedcbahgfedcbahgfedcba6-4-3-1-2-ihgfedcbac=c-c(o)-ch 3ch-chch-cxf fu un nc ct ti io on na al l g gr ro ou up p i in nt te er rc co on nv ve er rs si io on nc=cc cc=cc crch 2 -so 2 phrc chc cc-nh 2 ; c-no 2c-ohc(or) 2 ; c(sr) 2c=c-or; c=c-src cc nc=n-oh, c=n-hc=sc=oc=oc-c(

2、o)zc=cc=oc-ohc-xc-nc-hc-nc=oc-ohc-oc(o)rc-xc-och 2 orc-nh 2c-orc-hc-ohc=cc-hc(o)orc-(or) 2c-ohc-orc-choc-co 2 hc-cnc=cc=oc-sc-xc-ohc-hc=cjc(o)xh c njk c-hc-br8-c-xic-ohc-ohc(o)z dcbaedcbafc-nh 2c-hjcx-cyc cxc=ohgfic chrch(co 2 h)-ch 3-c(o)-ch 3oooxcrr"=chxjc oc-nh 2c-cn9-c-ch 3c-xaec=o 1-adry p

3、yridine: from cah 2 and distilled(an ester)triflatemesylatetosylatesooo rch 2 cf 3sooo rch 2 ch 3thiocarbonatedry pych 3ch 3ch 3oh(2). for 3" alcohol:lialh 4(1). for 1", 2" alcohol: c-h c-oh1- ihgfedcba c-choc-co 2 hc-cnc=cc=oc-sc-nh 2c-xc-ohc-ho cso phsnbu 3ch 3ch 3ch 3hn-bu 3 snh cs

4、o ph clo cso phrch 2 -hch 3 sooo rch 2ch 3 sooclrch 2 ohsteric okpurification textbook $ 30 / kgtoluenesulfonyl chloride (s)methanesulfonyy chloride (l) $ 30 / kgjc(o)xph 2 sihcl / incl 3 ph phhphohphjoc, 2021, 66, 7741.ii. ph 2 sihcl / incl 3i. p-tscl / lialh 4i. clc(s)oph / n-bu 3 snhphphocl 2 inc

5、l siph 2hvia:via:a unique lewis acid catalyst, acceleratedeoxgyenationincl 3indium trichlorideii. et 3 sih / lewis acid j. org. chem. 2021, 65, 6179joc, 2021, 65, 6179.chcl 2rt, 3 hr 1-bbu 3 snh: (l), easy to removeph 3 snh: (s), hard to removeme 3 snh: too volatile, toxic(aibn)n ncn cn- n 2cnazobis

6、isobutyronitrilen-busnhn-busnbrrn-busnbrrhrunstable in acid, form h 2 gas; stable in weak basenabh 3 cn: stable at ph 5-6hygroscopic, dried self, suggest: buy small amount each time(grignard reagent)h 2 o mg / et 2 ojoc, 1969, 34, 3923.hbrna / nh 3 ; li / nh 3 ; na / etohzn; fe; sn; mg(3). metal red

7、uction(2). hydride reduction(1). free radical reduction jacs, 1972, 94, 8905.c-h c-xaibnn-bu 3 snhhbrradical initiatornabh 4 / incl 3 / ch 3 cnradical reagentn-bu 3 snh / albnjacs, 2021, 124, 906.iiii nabh 3 cni lialh 4iiiii nabh 4iithl, 1969, 3095.joc, 1976, 41, 3064.iv libhet 3 (super hydride)n-bu

8、snhn-busn mechanism uncertain, probably radicalburn filter paper if dryraney nickel: ni - al alloy, suspensiontosylimidetosylamidejcs perkin trans i, 1973, 654.(3). lialh 4 / cucl 2nabh 4 / nicl 2nabhet 3 / fecl 2 (or cocl 2 , vcl 3 )(2). li / nh 3(1). raney ninso 2 arso 2 arrch 2rch 2 n so 2 ar- bu

9、hrch 2 nh so 2 arbulilialh 4rch 2 -hch 3 sooclrch 2 nh 2buli1-d1-cc-h c-slialh 4c-h c-nh 2rch 2 -hrch 2 nh 2hinsberg"s testradical mechanismweaker c-n bondchemistry: r-shr-s-r r 2 sor 2 so 2r-ss-rremove: hg + ; ni(1).(2).ar-hnano 2hclh 3 po 2ar-nh 2rch 2 nh 2 rch 2 nme 3r=ch 2 r-ch 3(4).x -rch

10、2 nme 3 oh -ag 2 ojoc, 1985, 50, 427.p-tsclnah nahp-tsclnh 2 clvia:nnh 2so 2 ararnahn nh ar n n ar ar-h- arso 2 h(3).ar-nh 2ar-hp-tscljoc, 2021, 66, 8293.arso 2 clraney nin hns meo 2 cch 2 pheto 2 con hnh meo 2 cch 2 pheto 2 c for acyclic, may c=c side productbasicneutralacidichhh -n n tsch 2 cl 2c=

11、oc-h 1-e(1). clemmensen reduction: zn-hg / hcl(2). thioketal: (3). wolff-kishner reduction:(5). tosylhydrazone reduction (shapiro reaction): (modified wolff-kishner reduction):)(6). enol derivatives: shsh/ bf 3 , ch 2 cl 2 / ranin 2 h 4 , oh - , heattsnhnh 2 / redlimit: for a-h compd.hhra(ni)bf 3 ,s

12、shhsshhothioketal: inert to lah; react with rani; smell terrible and stay long; discard shosesthioketalmajor side-product: drawback of the reactionn n- n 2oh -h n nhn n hoh -n nh 2n 2 h 4ohhnchcocf 3 sooo socf 3oc cotfh 2pto 2c ch hhtf 2 o / n/ h 2 / pto 2lah, nabh 4 : 2 group compete at stanford u.

13、b 2 h 6 : very flamable, fire if shoot out from syringeoob hbest suitable for aryl ketone (arcor); not good for conjugate ketone preparation: hgcl 2 into znred choice: meli; nabh 3 cn (good)pto 2 + h 2 = ptoh oc 6 h 13similar: sn / hcl(4). pd-c / hco 2 nh 4 : mild, efficientph phoph phsynthesis, 202

14、1, 16, 2370.hco 2 nh 4pd-c(7). et 3 sih / cf 3 coohphono 2ph no 2joc, 1973, 38, 2675.cf 3 coohet 3 sih hoohhhpto 2h 2hooh$ 50 / 25 gjoc, 1993, 58, 4979.syn-additionprepare isotopech 3 co 2 dhdc=c c-c-h1-f(1). h 2 / cat(2). hn=nh (diimide)(3). b 2 h 6 / rco 2 h, heatwilkinson"s catalyst: regiose

15、lective, prefer isolated double bondsoluble in org solvent, 9 ph groupstereoselcetive: same side as oh (due to h bond)catalyst: pd-cpto 2rh-c; rh-al 2 o 3 ; rhcl(pph 3 ) 3nioorhcl(pph 3 ) 3n 2 h 2 : unstable; generated in situ from quot;deadquot; (diethyl azodicarboxylate) or from: n 2 h 4 + h 2 o 2

16、 ; n 2 h 4 + cu(ii) + o 2 ; nh 2 oh + nh 2 oso 3via: hb rrn n co 2 et eto 2 cn n co 2 h ho 2 coh - 2 co 2n noohoohn n h h- n 2c crrrrc crrrrh hjcs, pt1, 1986, 546.ooco 2 meooco 2 merhcl(pph 3 ) 312 hrjacs, 1979, 101, 7020.nrnrh 2 , pto 2tfa , 60 r = nhac , nh 2joc, 2021, 67, 7890.in acetic condition

17、benzene(4). n-bu 2 sni / mgbr 2 -et 2 o / h 3 o +oetoh 3 o +oetomgbr 2 -et 2 on-bu 2 snijoc, 2021, 66, 8690.osnhoetir rooetsnirh rvia:not radical mech. pyridinium betainesolventnphph phrr hnphph phrr co 2- co 2b.p. 230 chighly toxic, cancer suspected agent?= hmpt: hexamethylphosphoric triamide (me 2

18、 n) 3 p=otoxic?characteristcs: ir, cmrwhich is d + ?c c r nnot quite same: not for h -e -co 2 hco 2 h(3). organic electrochemistryb-co 2 (1). particular structure: c-h1-g(1). k / al 2 o 3 k / hmpa(2). na / nh 31-h(2). normal structure: socl 2 / phseh / n-bu 3 snhc c njoc, 1980, 45, 3227cn: x (pseudo

19、 halogen), form kcn, nacn with ia elementshmpa: hexamethylphosphoramide (me 2 n) 3 p=oyes for white mouse, uncertain for humanmodified to: nnoc co 2 h c-hcoseph rch 2 rch 2 hcooh rch 2cocl rch 2phsehn-bu 3 snh socl 2(radical mechanism?)other cl sources: pcl 5 ; (cocl) 2oxalyl chlorideorganoselenium

20、chemistryohoro 1-icho c-h(1). rhcl(pph 3 ) 3 (wilkinson"s cat)(2). rh(dppd) 2 + cl -oxidative additionrearrangementreductive eliminationrhpph 3pph 3 cclo+ r hrhpph 3pph 3 croclhrhpph 3pph 3clhr cor cohrhpph 3pph 3cl- pph 3clrhpph 3pph 3 pph 3dppd = ph 2 p-ch 2 ch 2 -pph 21-jc(o)x -ch 3r clor ch

21、 3hsiet 3 / b(c 6 f 5 ) 3joc, 2021, 66, 1672. oooohalcl 3lialh 4activator / hydride sourceh och 3hcloch 3och 3och 3rch 2 oroorrororrch 2 och 2 ch 2 oh(3). alcl 3 / lialh 4(2). hcl / nabh 3 (cn)(1). hn / hsicl 3rc-(or) 2 rc-or 2-bsiphphclsich 3ch 3clch 3 sich 3ch 3clnnh/ tbdms-cltbdps-clet 3 n / tms-

22、clacid: h 2 so 4h 3 po 4bf 3 -et 2 orc-och 2 ch=ch2rc-ocph 3 = rc - otrrc-otburc-och 3rc-osir 3rc-och 2 ph = rc-obzl = rc-obni. willianson synthesis ok: si - cl bond longii. stability of silyl in acid/base: rc-o-tbdps gt; rc-o-tbdms gt;gt; rc-o-tbsiii. abbrev.: tbdms = tert-butyl-dimethylsilyl = tbs

23、 = silyl group:(ro-tr)trityl group: (tirphenylmethyl)i. s n 1 reactionii. abbreviation: triphenylmethyl = trityl = -cph 3 = -triii. advane: high mw, easy to handle (small amount become large amount)base brwillianson synthesis (base, s n 2) not work: elimination side-product with baset-butyl group:i.

24、 abbreviation: benzyl = phch 2 = bzl = bnii. deprotecting: h 2 / pd-cphch 2 -clphch 2 -br: reactivity goodphch 2 -i: reactivity better than phch 2 br, generated in situ, phch 2 br + naiphch 2 -x: benzyl- group:i. williamson ether synthesis, s n 2 typeii. not a good protecting group, too stable to co

25、nvert back to alcoholme group:ch 3 -x: ch 3 i; ch 3 oso 2 r; (ch 3 ) 3 o + bf 4 - , (ch 3 ) 2 so 4base: nah, n-buli, ag 2 o(4). t-bu: acid cat / (3). allyl: base / br(6). silyl: et 3 n / r 3 sicl(5). trityl: py / ph 3 c-br(2). phch 2 -: base / phch 2 -xapplication: for protecting groupedcba 2-rc=crc

26、-hrc(o)orrc-(or) 2rc-ohrc-orrc-oh rc-or(1). me: base / ch 3 -x2-a(7). acetal / ketal: (see 3e)f rc-cngenerate h 2 , or butane gasjoc, 1988, 53, 2985.trimethyloxonium tetrafluoroboratejcs, 1930, 2166.(8). arf / csfrohfno 2rono 2aromatic substitution reactionusually contain no 2 , f as leaving groupcs

27、f see mech-13hvi 2 / pb(oac) 4 o oho ihohoilimit: for 56 ring neighboring oh group(1). i 2 / pb(oac) 4 / hvradical mechanism: sicl 3t-buorani with c=sjoc, 1983, 48, 1127.joc, 1974, 39, 2470.ranilawesson reagentso ooo p 4 s 10tbu-oo-tbuhclooor coor2-crc-or2-drc-orrc-h(1). hv / hsicl 3(2). hcl / tbu-o

28、o-tbu(3). lawesson reagent / rani(4). bf 3 / nabh 4pspsssoch 3ch 3 oooooararoo ararbf 3nabh 4lawesson reagent(2). organoelectro chemistry: e - / pt, r 4 nots nohphnophe / ptr 4 nots(79 %)nohphr"r"mgbrangew chem int eng., 1964, 8, 525.limit for: lactonehnnhnh 2oh hhnnhnh 2ooch 3 ncs(3). ncs

29、 / meohmeohjoc, 2021, 67, 4498.limit: for allylic alcohol c-c-or2-ec cc conabh 4oetco 2 etohco 2 eth hohhohooi. hg(ococf 3 ) 2 , roh / nabh 4i. peracidii. via halohydrin: hobr, h 2 o / k 2 co 3iii. sharpless asymmetric epoxidation: t-buooh, ti(oipr) 4 / (+)-diethyl tartratehg(o cocf 3 ) 2oomcpbah 2

30、ohobrbr brohtrans-diaxial attack!olimit for allyl alcohol, high e.e.sharplessstereoselectiveracemic productshg o+cocf 3racemic productshobr generation: nbs + h 2 o + dmsoooconversion: hoacohoacoso 2 meoacetohc=c-orc=c-orc-c-orc cc cc cc co2-e. 12-e. 22-e. 3ii. hchoprins rxnoso 2 meoho oohoh ohhcho (

31、aq)o ovia:h 2 o hchosynthesis, 1980, 871.co 3 hco 3 hclcf 3 co 3 hco 3 hco 2 hgood resultperoxybenzoic acidmcpba(m-chloroperoxybenzoic acid)stable solid, 85 % (contain mcba) for safetyperacid:iv. t-buooh, mo(co) 6v. khso 5vi. h 2 o 2 , t-buoh, mnso 4 / nahco 3 , ph 8jacs, 2021, 123, 2933.ho 2 cho 2

32、conew, cheap, simple, green chemistrypotassium hydrogen preoxideconvenient, inexpensive, powerful. joc, 1980, 45, 4758. joc, 1982, 47, 2670.oohoobr 2via:br 2 / rohoobrhheterocyclic chem, 1990, 27, 583.c-c-or 2-f c n croh / hclet c n et coetoetoetetohhcljacs, 1942, 64, 1825.(+)-diethyl tartratechiral

33、 sourcejoc, 2021, 66, 521. c-ohc-hc-orc-nh 2c-x3- abcd3-ac-oh c-hoh(1). phi(oac)-o 2 -mn(tpp)(2). organic electrochemistryphi(oac)-o 2 -mn(tpp)jacs, 1983, 105, 3515.jacs, 1983, 105, 2920.no 2nh 2ohe -h 2 o(3). x 2 / hv / oh -indirecthohohoohhoh3-a. 13-a. 23-a. 3hroseorohsehoorseohrohse(oh) 2h 2 orhr

34、ohseo 2jacs, 1972, 94, 7154.seo 2for allyl h:(1) me 3 sicl / mpcba/h 3 o +(2). o 2 , lda, (eto) 3 proco 2 rroco 2 roho ororoopoetoetvia:jacs, 1975, 97, 6909.phophosime 3ophosime 3phosime 3ohohphooh1. me 3 siclmcpbajoc, 1975, 40, 3427.h 3 oo 2 , lda,(eto) 3 pphophooh2. mcpbame 3 siclihgfec=oc-ohc-oc(

35、o)rc-och 2 orc=cjc o (1). me: application: deprotecting(2). phch 2 - (5). trityl: (6). silyl: (3). allyl: (4). t-bu: rc-och 2 ph = rc-obzl = rc-obnrc-osir 3rc-och 3rc-otburc-ocph 3 = rc-otrrc-och 2 ch=ch 2c-oh c-orni. tmsiii. bf 3 -et 2 o / r-sh (or hs-ch 2 ch 2 -sh)iii. bbr 3 / ch 2 cl 2 , 0-10 c/

36、lii, heatvi. rch 2 -ohrch 2 -o-sime 3me 3 si-irch 2 och 3sime 3- ch 3 irch 2 -o-ch 3i - i -rch 2 -o-ch 3rch 2 och 3bf 3bf 3- rsch 3rshrch 2 -ohoch 3oh+heat- ch 3 cli. h 2 / pd-cii. cncnclcloo, oh -ooh- tolueneoh -oho c och 3oo ch 2 och 3h 2 / pd-co ch 2rhcl(pph 3 ) 3 , h 3 o +- etcho- ph 3 cohhoacho

37、hho cph 3- me 3 ccf 3 co 2 hoh oh 3 o +rhcl(pph 3 ) 3hohhohoi. tfa (cf 3 co 2 h)ii. hbr / hoaciii. tms-ii. hoac: weak acid: good leaving groupii. h 2 / pd-c: reserve, too strong, might affect other groupneed stronger acidi. f - : hf, py-h + f - ; n-bu 4 n + f -ii. mild base: not for tbdpsiii. mild a

38、cid: only for tms, not for tbdms, tbdps-sime 3-sibume 2-sibuph 2si - f: 140 kcal/molif hobr: ok for tmdms joc, 1987, 52, 4973.ococf 3+joc, 1973, 38, 3224.iv. alcl 3 / rshthl, 2021, 42, 9207.meo co 2 meho co 2 mech 3 (ch 2 ) 11 shodorlessalcl 3v. / heatcl -nh3-b nh cl -triphenylmethylorganic base: tm

39、gorch 3 cnnhnnohr = tbdms, tbdps, actmg1h1,1,3,3-tetramethylguanidinetmg:organic letters, 2021, 5, 209. 3-c(1). hno 2 / h 3 o +c-ohc-x(1). oh -(2). ko 2 / dmso3-d c-oh c-nh 2not practically useful: r-oh cheaper than r-xjoc, 1975, 40, 1678.(2). na 2 fe(cn) 5 (no) / k 2 co 3 / h 2 ono +h 3 o +ohn 2 +

40、x - nh 23-er-oh r-oc(o)r(1). symmetry:ketal: use h 3 o +acetal: use h 3 o +(2). unsymetry: ro-momro-memro-mtmro-thpmeoh+h 3 o +ohhomeome+oh hoh 3 o +oo oi. h 3 o + ; ii. hcl / meoh; iii. bbrme 2p-tsoh / meoh i. h 3 o + ; ii. znbr 2 / ch 2 cl 2 ; iii. bbrme 2hgcl 2 / ch 3 cn (aq.)actually, acetal exc

41、hange rather than hydrolysish 3 o +ro-hro-hro-hro-hro-ch 2 sch 3ro-ch 2 och 3r ooso 3 hoch 3 och 2 clch 3 och 2 ch 2 och 2 clch 3 sch 2 clp-tsohop-tsohcsa (camphorsulfonic acid)(p-toluenesulfonic acid)so 3 h ch 3or csaro-mom highly toxic, world top 10 killer, discardnot toxicnot dangerousthp: tetrah

42、ydropyranro-ch 2 och 2 ch 2 och 3joc, 1984, 49, 3912.(3). ag 2 o / h 2 oh 3 o +h 3 o +h 3 o +thl, 1975, 3183.joc, 1986, 51, 3913. ro 2 c(ch 2 ) 3 chrnh 2ro 2 c (ch 2 ) 3 chrohna 2 fe(cn) 5 (no)k 2 co 3 / h 2 o 3-f(1). base: khco 3 (or k 2 co 3 , nh 3 ) / meoh; naoh (1 %, or 0.5 n)(3). red: (2). acid

43、: h 3 o +pph 3 / dead / rco 2 h / oh -3-gr" c o ror ohc oh c ohmitsunobu inversion synthesis, 1981, 1.joc, 1987, 52, mon esters: formate = hco 2 r - khco 3 (or k 2 co 3 , or nh 3 ) / meohtrifluoroacetate = cf 3 co 2 r - khco 3 (or k 2 co 3 , or nh 3 ) / meohacetate = ch 3 co 2 r = roac - khco 3

44、 (or k 2 co 3 , or nh 3 ) / meohbenzoate = phco 2 r = robz - naoh (1 %) / meohpivalate = tbu-co 2 r = ropv - naoh (0.5 n) / etoh(or k 2 co 3 / meoh)meohmeohp-tsohlahhcloooho ohohoohooooselectivity:pph 3 / deadr-o-h*phco 2 hn nh co 2 et eto 2 cp ph o rphphoh -ph c orohophco 2 h*hopph 3n nh co 2 et et

45、o 2 cpph 3roheto 2 c n n co 2 eti lialh 4ii. naalh 2 (och 2 ch 2 och 3 )ch 3 o 2 cco 2 ch 3hoohnaalh 2 (och 2 ch 2 och 3 ) 2c 6 h 6 , r.t.hydride:electron:na / nh 3 agiee, 2021, 41, 3028. regioselectivity determined by reactivity. reactivity: ald gt; ketone gt; estergenerate acetoneopposite to oppen

46、auer oxidationjcs, 1969, 1653. jcs, 1970, 785.jacs, 1972, 94, 7159.oircl 4al(oipr) 3o+aloiproiprohlahoooohhho al(oipr) 2ircl 3ohhohhohlah - almost all: ald, ketone, acie, ester, acyl x, anhydridenabh 4 - not for acid, ester (but libh 4 work for ester)b 2 h 6 - not for ester, acyl x, anhydride; from

47、top: lialh 4 ; nabh 4 ; na / nh 3al (oipr) 3 / iproh - meerwein-pondorf-verley rxnircl 4 / iproh / p(ome) 3 - henbest rxnlibh(secbu) 3 - h. c. brownfrom bottom:c oh c o(2). stereoselective: (1). regioselective: 3-h(3). hcho reagent: me chomeohhchokohjacs, 1935, 511, 903.ch 3 choc(ch 2 oh) 4hchoca(oh

48、) 2org.syn, 1925, 4, 53.hcho / kohhcho / ca(oh) 2synthesis, 1994, 1007.phno 2ophno 2h ohbh 3 / sme 2joc, 2021, 66, 7514.joc, 2021, 68, 2030.oohbh 3 / thfreflux 5 d99.5 % transsolvent: thf, sme 2c oh c o3-ir 3 b, hoch 2 ch 2 oh / h 2 o 2 / naohjoc, 1986, 51, 4925.c o r b c orrr 3 bb crrror b corrr 3

49、c b ohoch 2 ch 2 ohr 3 c booh 2 o 2ohr 3 c booo o ho boor 3 ch 2 or 3 c oho ohohnabh 4 / cecl 3nabh 4+99%trace51%49%hjacs, 1978, 100, 2226.luche reductionthl, 2021, 41, 5631.influence of the lanthanide on the regiochemistry p pr ra ac ct ti ic ce e 3-koohohohohoohohohohohpd-ch +oohohohoho ohohohohoh

50、h 2pycro 3ph 3 c-cloh otrobnobnbnoobnlahh 3 o +oh ohobnobnbnoobnphch 2 -brohoobnobnbnoobn hoohbnoobnobnobno omeobnobnbnoobnmeoho omeohohhooho ohohohhoohchemistry:hemiacetalroh robnrohrohrotr rohjoc, 1967, 32, 3452.1", 2" alcoholo otrobnobnbnoobnh 2 o 2 : dangerous, skin whiten, metal decom

51、posehg (oac) 2 : toxic, hard to removeh 2 oohobr 2oh - (40%-60%)h 2 o 2hbhbb 2 h 6nabh 4h 2 ohg(oac) 2ch crr rh ohch crrohrhgoacrch crrc oh c c(3). b 2 h 6 , h 2 o 2 / oh - , h 2 o(2). hg(oac) 2 , h 2 o / nabh 4(1). h 3 o +3-jo o hbrrc oh c c3-j. 1c c3-j. 2 hydroboration: oxymercuration - demercurat

52、ion: hydration: c coh oh(1). kmno 4 / naoh(2). oso 4(3). h 2 o 2 /hco 2 h(4). na / etohohohohohcistrancis + tranjacs, 1945, 67, 1786.ann, 1949, 561, 165.jcs, 1946, 2988.cis n ch 3clhn ch 3clhme 2 nnnch 3hcln ch 3hhhnn ch 3hhn ch 3clhh +ncsn ch 3cl nhch 3nhchome 2 nntsocnhchotsodmfme 2 nhhcoohacohoac

53、tsclmeohk 2 co 3nhcho2. h 2 / pt1. lahr 3 c nh 2r c nr 2r c nhrr 3 c ohr 2 c ohrcohr c nh 2tertiarysecondaryprimarycompare nomenclature class:not a very useful reactionc-nc-hc-nc-xc-ohc=oc=c4- abcdefg4-ac-nc-h(1). nitrene insertion process: phi(oac) 2 / fe (tpp)cl(3). nitrogen cation radical (via ho

54、fmann - loeffler - frey)so 2 nh 2 ph ioacoac soonhsoon i phfe (tpp)clsoonh 2(insertion)tppn nn nphhcoohaconh 2me 2 nme 2 nnncsh 2 so 4hnjacs, 1959, 81, 5209.2. nan 3con n nn c o1. so 2 cl 2hoac h 2 on coohco 2nh 2ch 3cocho ohic n(2). phi=ntsnhtsphi ntsru catjoc, 2021, 65, 7858.c(o)xc-c(o)x rc n z rc nh 2nh 2nh 2rc no 2rc n 3rc n merc n cphrc n