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Химия

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Patai S., Rappoport Z. 1996 The chemistry of functional groups. The chemistry of amino, nitroso, nitro and related groups. Part 2 / 0683 745

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15. Photochemistry of amines and amino compounds

733

For the intermolecular interactions between N-methylphthalimide and alkenes, two reactions paths are possible183. The ﬁrst is the regioand stereocontrolled 2 C2 cycloaddition of the alkene to the C N bond to generate dihydrobenzazepinedione (equation 126), while the second is the electron transfer initiated addition(equation 127).

hν

(126)

hν

Me +

+ •

•

O −

NMe

Me +

NMe

OMe

CH2

(in MeCN)

(in MeOH)

(127)

Intramolecular

photocycloaddition

possible

for

the

bis-methacryl-

184

arylimide

(equation 128).

hν

NAr

(128)

(major)

734	Tong-Ing Ho and Yuan L. Chow
Both saturated or unsaturated thioimides and dithioimides				behave like thioketones
in their	photocycloaddition	reaction with	alkenes (equation 129) and		alkynes
(equation 130)185.
				Ph
	S			S
	S
		Ph		Ph	(129)
		+	hν		(129)
	NMe	+	hν	NMe
		Ph
	O			O
				Ph
	S			S
	S
	NMe + PhC CPh		hν	Ph	(130)
			hν	NMe
				NMe
	O			O

Dithioamides behave similarly186 (equation 131) but, in the presence of steric hindrance in addition to the thiocarbonyl groups, the photoaddition will become regioselective187 (equation 132). Intramolecular photocycloaddition will lead to the formation of strained polycyclic thietanes188 (equation 133). Hydrogen abstraction by the thioamide functional group is also possible189 (equation 134).

	Me			Me
S	N	S	S	N	S
S	N	S	S	N
		+	hν		(131)
		+			(131)
					(86%)
	S				S
Me		Me +	hν	Me	N Me
Me	N		hν	Me
	N

					(132)
	S				S

(50%)

	15. Photochemistry of amines and amino compounds			735
	Me
S		S
		S	Me
			Me
N	hν			(133)
		N
S		S
		(80%)
			Ph
	S		HS
			HS
	N	Ph	hν	(134)
	N	Ph		N
	S		O

Sulphenamides190 are photochemically active and undergo homolytic cleavage of the S N bond. The products are derived from the sulphurand nitrogen-centred free radicals (equation 135). Oxygen atom transfer from a neighbouring nitro group to the sulphur is also observed191 (equation 136).

NHMe

hν		+ PhS	NHMe
PhS N		+ PhS	NHMe
Ph	SPh		(135)
	SPh		(135)
	+	NHMe +	PhSSPh
Me		Me
S N	NMe2	O2 S N	NMe2
O2 N		H2 N
	hν
NO2		NO2

(136)

736	Tong-Ing Ho and Yuan L. Chow

Similarly to the sulphenamides, the photochemistry of isothiazole is initiated by the ﬁssion of the weakest S N bond192 (equation 137 and 138).

			H
			S	O
	hν	S •	S
S	hν	S •
N	O	•N	O	N
Ph		Ph		Ph
					(137)
				S
				O
				N
				Ph
	O			O
			hν
	N		Me	N•	Me
	S			S •
		O		O
		N		NH
		S		S
		H			Me
			Me	(60%)	Me
				(60%)
					(138)
The	photochemical	deprotection	of sulphonamides to	free amines is	synthetically

useful193. This process is caused by electron transfer from an electron-donating sensitizer such as 1,2-dimethoxybenzene or 1,4-dimethoxybenzene and the presence of reductants like ammonia or hydrazine is also required194 (equation 139).

	15. Photochemistry of amines and amino compounds			737
MeO			MeO
MeO
	N		hν	NH
MeO	N			NH
MeO	SO2	CH3	MeO
	CH2 Pr			CH2 Ph
				(100%)
				(139)

Extrusion of sulphur dioxide by a free radical mechanism can also lead to several ring-closing or ring-opening reactions. For example, intramolecular reaction of the enone 181 to the 3-substituted enone is accompanied by a phenyl shift195 (equation 140). Free radical ring closure may lead to the formation of useful heterocycles such as azetidine196 (equation 141) or carbazole197 (equation 142). In the absence of an external nucleophile such as n-butylamine, photochemical ring closure of sultam 182 affords a pyrrole. Trapping of the N S ruptured intermediate is also possible198 (equation 143).

O	R			O•	R
	N				N	•
	SO2 Ph		hν		SO2	•
			hν
			C6 H6
					Ph
	(181)
		O			O
			NR

(65%)

	CH2
	hν
	SO2
N	N
Me	Me

(140)

NHR

R = CHMe2

(60%)

(141)

738		Tong-Ing Ho and Yuan L. Chow
SO2	hν
	hν
N			(142)
N
Ph		N
Ph		H
		H
		hν
	SO2	SO2	N
N		NPh	N
N		NPh
Ph		(182)	Ph
Ph
		n-C4 H9 NH2	(60%)

CH2 SO2 NH-(C4 H9 )

NPh

(60%)

(143)

Ring expansion of the sulphonamide reaction199 (equation 144) demonstrates the ability of a ruptured sulphur-centred free radical to undergo 1,3-Fries type migration200 (equation 145). Sulphur dioxide extrusion may also provide a synthetic route to ˇ- lactams201 (equation 146).

					Me
		Me
				O2
O2				S
S	N				(144)
	N	hν			Me
		hν
	Me				N
	Me			N	H
N	Me				H
N	Me
					Me
SO2 Ph
RN	NHR			NHR
		SO2 Ph			(145)
hν			+		(145)
			+

SO2 Ph

15. Photochemistry of amines and amino compounds								739
O2	Ph
S	Ph
		hν			+			(146)
		hν
N
				N			N
				N			N
O			O			O

(major)

The amide functionality plays an important role in the physical and chemical properties of proteins and peptides, especially in their ability to be involved in the photoinduced electron transfer process. Polyamides and proteins are known to take part in the biological electron transport mechanism for oxidation reduction and photosynthesis processes. Therefore studies of the photochemistry of proteins or peptides are very important. Irradiation (at 254 nm) of the simplest dipeptide, glycylglycine, in aqueous solution affords carbon dioxide, ammonia and acetamide in relatively high yields and quantum yield (0.44)202 (equation 147). The reaction mechanism is thought to involve an electron transfer process. The isolation of intermediates such as N-hydroxymethylacetamide and N-glycylglycyl-methyl acetamide conﬁrmed the electron-transfer initiated free radical processes203 (equation 148).

COO−

hν

+ CO2 + NH3

H3 N

CH2

CH3 CONH2

(147)

−

hν

O•

NCH CNHCH C

• CH CNHCH

•

H3 NCH2 CNHCH2 C

•

CH3

CNHCH2 OH + CH3

CNHCH2 NHCH2

CNHCH2 CO2 H

(148)

Terminal

deamination

is also a

major step

gamma ray

reactions

with

aliphatic

oligopeptides in aqueous solution204. This conﬁrms that the amide group tends to react with the solvated electron. Ring opening of the pyrrolidine also occurs in the photolysis of pyrrolylglycine which is without a primary free amino group205 (equation 149).

		−			O
		O			O
+	H			hν
	H			hν
	N	C			H2 N(CH2 )4 CNHCH2 OH + CO2 (149)
	N	C			H2 N(CH2 )4 CNHCH2 OH + CO2 (149)
N	C	C	O
H	O	H2
	O

As for the photophysical aspects for the bio-mimic photoinduced electron transfer systems, studies on amides206 and amino acid assemblies207 have recently begun to be popular.

740	Tong-Ing Ho and Yuan L. Chow

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